Hydrochloric Acid → {4-[(Methanesulfonyl)amino]phenyl}acetic acid

HRID 1386473Notes

Reaction equation

HRID 1386473 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].Cl>O>[CH3:18][S:19]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]([OH:17])=[O:16])=[CH:12][CH:13]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 145334-Aminophenylacetic acidHCID 31297Methanesulfonyl chloride

Product 1

HCID 2773887{4-[(Methanesulfonyl)amino]phenyl}acetic acidYield 58.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

In a solution containing 5.44 g (53 mmol) of sodium carbonate in 36 ml of water, 3.2 g (20 mmol) of 4-aminophenylacetic acid are dissolved, 1.7 ml (2.48 g, 22 mmol) of methanesulfonyl chloride are added in one portion and the mixture is heated at 85° C. for 4 hours. After cooling down and acidifying the reaction mixture to pH 3 with concentrated hydrochloric acid, the mixture is cooled in the refrigerator overnight, filtered, washed with water and dried to obtain 2.7 g of a crude product, which is recrystallized from 6 ml of hot water to give 2.40 g of the title substance as beige laminar crystals; yield: 53%, m.p.: 145-147° C.

Workup

  1. dissolutionare dissolved
  2. temperatureAfter cooling down
  3. temperaturethe mixture is cooled in the refrigerator overnight
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-528e5952583b41028e97c1f8139d652d
Source dataset
uspto-grants-2001_07
Patent number
US06265445B1

Reaction notes

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