furan-2-ylmethylthiourea

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

Procedure: 2-[(Furan-2-ylmethyl)-amino]-thiazole-4-carboxylic acid (220 mg) was prepared according to General Procedure B using furan-2-ylmethyl-thiourea (156 mg) and 3-bromo-2-oxo-propionic acid (167 mg).

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

Procedure: N-furfurylthiourea (0.82 grams, 0.005 moles) and α-bromopropiophenone (1.07 grams, 0.005 moles, Aldrich Chem. Co.) in 11 ml absolute ethanol were heated to reflux temperature under nitrogen for 3 hours. After cooling to room temperature, the solvent was removed under vacuum to give a thick brown oil, which was triturated with five 35 ml portions of refluxing ethyl acetate. The ethyl acetate was reduced in volume to about 25 ml and cooled to room temperature. The precipitated solids were filtered, washed with ethyl acetate and vacuum dried over phosphorous pentoxide, yielding 0.585 grams (33%) of 2-furfurylamino-5-methyl-4-phenyl-thiazole hydrobromide, m.p. 150°-153° C. to reflux temperature under nitrogen for 3 hours the solvent was removed under vacuum to give a thick brown oil, which was triturated with five 35 ml portions of refluxing ethyl acetate cooled to room temperature The precipitated solids were filtered washed with ethyl acetate and vacuum dried over phosphorous pentoxide

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

Procedure: Furfurylamine hydrochloride (33.46 grams, 0.250 moles) and ammonium thiocyanate (38.14 grams, 0.501 moles) in 71 ml bromobenzene were heated under nitrogen at reflux temperature for 20 minutes and then cooled to room temperature. The reaction mixture was mixed with a solution of 125 ml water and 100 ml ethyl acetate and left at room temperature overnight. The mixture was then diluted to give 500 ml ethyl acetate and 350 ml water and the aqueous layer separated. The organic layer was washed with water and dried over sodium sulfate. After filtration, the organic layer was evaporated to dryness and bromobenzene removed under vacuum. The resulting solids were ground in a mortar and pestle and the fine particles stirred in diethyl ether to remove residual bromobenzene. The solids were then filtered, washed with diethyl ether and vacuum dried over phosphorus pentoxide, yielding 12.06 grams (30%) of N-furfurylthiourea, m.p. 80°-91° C. Recrystallization from benzene gave yellow needles, m.p. 98°-100° C. at reflux temperature for 20 minutes The mixture was then diluted the aqueous layer separated The organic layer was washed with water dried over sodium sulfate After filtration the organic layer was evaporated to dryness and bromobenzene removed under vacuum to remove residual bromobenzene The solids were then filtered washed with diethyl ether and vacuum dried over phosphorus pentoxide