1-methyl-1-phenylthiourea

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

Procedure: A mixture of 1-methyl-1-phenyl-thiourea (5.03 g, 30.3 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.4 mL, 31.8 mmol) in ethanol (18 mL) was refluxed for 20 h before it was cooled to room temperature and concentrated in vacuo. It was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a brown solid (7.39 g): MS: (+) m/z 277.0 (M+1). was refluxed for 20 h before it concentrated in vacuo It was partitioned between ethyl acetate and saturated sodium bicarbonate the organic layer was washed with brine dried over anhydrous sodium sulfate concentrated in vacuo

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

Procedure: A mixture of 1-methyl-1-phenyl-thiourea (5.03 g, 30.3 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.4 mL, 31.8 mmol) in ethanol (18 mL) was refluxed for 20 h before it was cooled to room temperature and concentrated in vacuo. It was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a brown solid (7.39 g): MS: (+) m/z 277.0 (M+1). was refluxed for 20 h before it concentrated in vacuo It was partitioned between ethyl acetate and saturated sodium bicarbonate the organic layer was washed with brine dried over anhydrous sodium sulfate concentrated in vacuo

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

Procedure: A solution of 10 g (60 mmol) of N-methyl-N-phenylthiourea in 100 mL of toluene was treated with 7.2 mL (63 mmol) of chloroacetaldehyde dimethylacetal and heated at reflux for 12 h. The solvent was removed in vacuo and the residue purified by flash chromatography eluting with a linear gradient of 30% EtOAc in hexane to 80% EtOAc in hexane to deliver the title compound. MS (M+H)+ 191. heated at reflux for 12 h The solvent was removed in vacuo the residue purified by flash chromatography eluting with a linear gradient of 30% EtOAc in hexane to 80% EtOAc in hexane

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

Procedure: A solution of 10 g (60 mmol) of N-methyl-N-phenylthiourea in 100 mL of toluene was treated with 7.2 mL (63 mmol) of chloroacetaldehyde dimethylacetal and heated at reflux for 12 h. The solvent was removed in vacuo and the residue purified by flash chromatography eluting with a linear gradient of 30% EtOAc in hexane to 80% EtOAc in hexane to deliver the title compound. MS (M+H)+ 191. heated at reflux for 12 h The solvent was removed in vacuo the residue purified by flash chromatography eluting with a linear gradient of 30% EtOAc in hexane to 80% EtOAc in hexane

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

Procedure: When using, instead of 4-methoxyphenyl-thiourea of Examples 89 and 90, equivalent amounts of N-phenyl-N'-methyl-thiourea or N-phenyl-N-methyl-thiourea, the other conditions remaining the same, 2-methylamino-benzthiazole (m.p. 137° C.) or 3-methyl-2-imino-benzthiazoline (m.p. 122°) is obtained in an equally good yield and in a high purity.

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

Procedure: When the reaction is carried out as described in Example 23 with the exception that instead of N-ethyl-N-phenylthiourea an equimolar amount of N-methyl-N-phenylthiourea is used, 3-methyl-2-iminobenzthiazoline melting at 122° C. is obtained in a yield of 95.6% and with an equally good purity.

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

Procedure: A mixture of 1-methyl-1-phenyl-thiourea (5.03 g, 30.3 mmol) and 2-chloro-3-oxo-butyric acid ethyl ester (4.4 mL, 31.8 mmol) in ethanol (18 mL) was refluxed for 20 h before it was cooled to room temperature and concentrated in vacuo. It was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a brown solid (7.39 g): MS: (+) m/z 277.0 (M+1). was refluxed for 20 h before it concentrated in vacuo It was partitioned between ethyl acetate and saturated sodium bicarbonate the organic layer was washed with brine dried over anhydrous sodium sulfate concentrated in vacuo

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

Procedure: A solution of 10 g (60 mmol) of N-methyl-N-phenylthiourea in 100 mL of toluene was treated with 7.2 mL (63 mmol) of chloroacetaldehyde dimethylacetal and heated at reflux for 12 h. The solvent was removed in vacuo and the residue purified by flash chromatography eluting with a linear gradient of 30% EtOAc in hexane to 80% EtOAc in hexane to deliver the title compound. MS (M+H)+ 191. heated at reflux for 12 h The solvent was removed in vacuo the residue purified by flash chromatography eluting with a linear gradient of 30% EtOAc in hexane to 80% EtOAc in hexane