1,2,3,4-tetrahydronaphthalen-1-ylurea

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.5 g of 1,2,3,4-tetrahydro-1-naphthylurea in 50 ml of 50% aqueous acetic acid is cooled to below 5° C and 6.0 g of ceric ammonium nitrate added. After 5 minutes the mixture is diluted with water and extracted with 3 × 5 ml of ethyl acetate. The extracts are combined and evaporated to dryness to afford the crude title product. extracted with 3 × 5 ml of ethyl acetate evaporated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7.6 grams (0.04 mole) of (1,2,3,4-tetrahydro-1-naphthyl)urea, 2.0 grams of sodium hydroxide and 2.2 grams of para-formaldehyde in 150 ml. of methanol is stirred at reflux temperature for 10 hours. The reaction mixture is cooled and neutralized with dry ice. The solvent is evaporated at reduced pressure. The residue is treated with water, the mixture filtered, and the filter cake washed with water and dried to give 8.2 grams of product, melting point 124.5° C. to 127.5° C. Recrystallization from methyl isobutyl ketone gives the analytical sample, melting point 136° to 138.5° C. at reflux temperature for 10 hours The reaction mixture is cooled The solvent is evaporated at reduced pressure The residue is treated with water the mixture filtered the filter cake washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7.6 grams (0.04 mole) of (1,2,3,4-tetrahydro-1-naphthyl)urea, 2.0 grams of sodium hydroxide and 2.2 grams of para-formaldehyde in 150 ml. of methanol is stirred at reflux temperature for 10 hours. The reaction mixture is cooled and neutralized with dry ice. The solvent is evaporated at reduced pressure. The residue is treated with water, the mixture filtered, and the filter cake washed with water and dried to give 8.2 grams of product, melting point 124.5° C. to 127.5° C. Recrystallization from methyl isobutyl ketone gives the analytical sample, melting point 136° to 138.5° C. at reflux temperature for 10 hours The reaction mixture is cooled The solvent is evaporated at reduced pressure The residue is treated with water the mixture filtered the filter cake washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.5 g of 1,2,3,4-tetrahydro-1-naphthylurea in 50 ml of 50% aqueous acetic acid is cooled to below 5° C and 6.0 g of ceric ammonium nitrate added. After 5 minutes the mixture is diluted with water and extracted with 3 × 5 ml of ethyl acetate. The extracts are combined and evaporated to dryness to afford the crude title product. extracted with 3 × 5 ml of ethyl acetate evaporated to dryness

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 0.5 g of 1,2,3,4-tetrahydro-1-naphthylurea in 50 ml of 50% aqueous acetic acid is cooled to below 5° C and 6.0 g of ceric ammonium nitrate added. After 5 minutes the mixture is diluted with water and extracted with 3 × 5 ml of ethyl acetate. The extracts are combined and evaporated to dryness to afford the crude title product. extracted with 3 × 5 ml of ethyl acetate evaporated to dryness

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-benzoyl-3-(1,2,3,4-tetrahydro-1- naphthyl)urea (2.0 g) and aqueous sodium hydroxide (1N; 20 ml) is stirred and heated at reflux for 2.75 hours. The mixture is then cooled in ice and the product is collected and washed with water to afford 1.15 g of the title compound, m.p. 204° to 207° C. heated at reflux for 2.75 hours The mixture is then cooled in ice the product is collected washed with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7.6 grams (0.04 mole) of (1,2,3,4-tetrahydro-1-naphthyl)urea, 2,0 grams of sodium hydroxide and 2.2 grams of para-formaldehyde in 150 ml. of methanol is stirred at reflux temperature for 10 hours. The reaction mixture is cooled and neutralized with dry ice. The solvent is evaporated at reduced pressure. The residue is treated with water, the mixture filtered, and the filter cake washed with water and dried to give 8.2 grams of product, melting point 124.5° C. to 127.5° C. Recrystallization from methyl isobutyl ketone gives the analytical sample, melting point 136° C. to 138.5° C. at reflux temperature for 10 hours The reaction mixture is cooled The solvent is evaporated at reduced pressure The residue is treated with water the mixture filtered the filter cake washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 7.6 grams (0.04 mole) of (1,2,3,4-tetrahydro-1-naphtyl)urea, 2.0 grams of sodium hydroxide and 2.2 grams of para-formaldehyde in 150 ml. of methanol is stirred at reflux temperature for 10 hours. The reaction mixture is cooled and neutralized with dry ice. The solvent is evaporated at reduced pressure. The residue is treated with water, the mixture filtered, and the filter cake washed with water and dried to give 8.2 grams of product, melting point 124.5° C. to 127.5° C. Recrystallization from methyl isobutyl ketone gives the analytical sample, melting point 136° to 138.5° C. at reflux temperature for 10 hours The reaction mixture is cooled The solvent is evaporated at reduced pressure The residue is treated with water the mixture filtered the filter cake washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the manner described in Example 60, 1-benzoyl-3-(4,5,6,7-tetrahydrobenzo[b]thien-4-yl)urea and 1-benzoyl-3-(1,2,3,4-tetrahydro-1-naphthyl)urea are hydrolyzed to afford 4,5,6,7-tetrahydrobenzo[b]thien-4-ylurea, m.p. 204.5° C. to 208.5° C., and 1,2,3,4-tetrahydro-1-naphthylurea, m.p. 212° C. to 214° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,2,3,4-tetrahydro-1-naphthylurea (1.9 g), cobaltous acetate tetrahydrate (1.08 g), 30% hydrobromic acid in acetic acid (0.9 ml) and a 1:1 mixture of methyl ethyl ketone: acetic acid (30 ml) is shaken in a pressure vessel under 31 psig of oxygen for 7.5 hours. The vessel is then vented, the contents are mixed with an equal volume of water and extracted with chloroform (2×25 ml). The combined chloroform extracts are dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo to afford 2.34 g solid. The solid is washed with cold methanol (30 ml) to afford 0.75 g of title compound, m.p. 210° C. to 214° C. extracted with chloroform (2×25 ml) The combined chloroform extracts are dried over anhydrous magnesium sulfate evaporated to dryness in vacuo