Water → methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate

HRID 1597808Notes

Reaction equation

HRID 1597808 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH3:11])=[O:9].[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([CH3:30])[CH:24]=1.O>CN(C)C=O>[S:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[CH2:21][O:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:8](=[O:9])[O:10][CH3:11])=[C:25]([CH3:30])[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 9354004-(Benzo(D)Thiazol-2-Ylmethoxy)-2-Methylaniline

Product 1

HCID 18932257methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamateYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

82.5 ml of pyridine and 18.9 ml of methyl chloroformate were added to a solution of 55.0 g of 4-(benzothiazol-2-ylmethoxy)-2-methylaniline [prepared as described in step (b) above] in 400 ml of dimethylformamide cooled in an ice-water bath and the resulting mixture was stirred at the same temperature for 2 hours. At the end of this time, the reaction mixture was poured into water resulting in the precipitation of a crystalline solid which was washed with water and then further washed with diethyl ether to give a crude crystalline solid. This was recrystallised from a 4:1 by volume mixture of tetrachloromethane and acetone to give 36.2 g (yield 54%) of the title compound as a solid having a melting point of 147° to 149° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. washwas washed with water
  3. washfurther washed with diethyl ether
  4. customto give a crude crystalline solid
  5. customThis was recrystallised from a 4:1 by volume mixture of tetrachloromethane and acetone

Sources & evidence

ORD record
ord-40fed1140ea944a284d72e6013d21908
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

Loading…