Water → 3-methyl-4-(p-toluenesulfonamido)phenyl N-methylcarbamate

HRID 2072432Notes

Reaction equation

HRID 2072432 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][NH:13][C:14](=[O:24])[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([CH3:23])[CH:17]=1.O>N1C=CC=CC=1>[CH3:12][NH:13][C:14](=[O:24])[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])=[C:18]([CH3:23])[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 25072Aminomatacil

Product 1

HCID 545265613-methyl-4-(p-toluenesulfonamido)phenyl N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-Toluenesulfonyl chloride (2.1g., 0.011 mole) was added portionwise to a solution of 3-methyl-4-aminophenyl N-methylcarbamate (1.8g., 0.01 mole) in pyridine (15 ml.). An exotherm to about 45° C. resulted and warming was continued at 48° C. for a short time. An excess of water was added and upon stirring and cooling, the product crystallized. The filtered product (3.1g.) was recrystallized from ethanol/water to give material with m.p. 181°-83.5° C.

Workup

  1. customAn exotherm to about 45° C. resulted
  2. temperaturewarming
  3. customwas continued at 48° C. for a short time
  4. temperaturecooling
  5. customthe product crystallized
  6. customThe filtered product (3.1g.) was recrystallized from ethanol/water
  7. customto give material with m.p. 181°-83.5° C.

Sources & evidence

ORD record
ord-ffe38e82552d4040a6eda232c8765293
Source dataset
uspto-grants-1977_09
Patent number
US04051254

Reaction notes

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