Hydrochloric Acid → 2-(4-fluorophenylsulfonamido)acetic acid

HRID 378914Notes

Reaction equation

HRID 378914 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][C:14]([OH:16])=[O:15].C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][CH2:13][C:14]([OH:16])=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 7302692-(4-fluorophenylsulfonamido)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-fluoro-benzenesulfonyl chloride (9.68 g, 0.497 mol), glycine (4.48 g, 0.0598 mol), and sodium carbonate (16.99 g, 0.160 mol) in water (60 mL) was stirred at room temperature for 42 hours. The mixture was carefully acidified to pH 8 to 9 with concentrated hydrochloric acid, and washed 2 times with dichloromethane. The aqueous layer was acidified further to pH 2, and the resulting white suspension was extracted two times with ethyl acetate. The extracts were combined, washed with saturated sodium chloride solution, and dried over magnesium sulfate. The dried solution was rotary evaporated to give a white solid, which was dried in vacuo; yield 4.7 g (41%), mp=154.0-155.5° C.

Workup

  1. washwashed 2 times with dichloromethane
  2. extractionthe resulting white suspension was extracted two times with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe dried solution was rotary evaporated
  6. customto give a white solid, which
  7. customwas dried in vacuo

Sources & evidence

ORD record
ord-2bd597aad4704869a674cf570bdc5a61
Source dataset
uspto-grants-2001_10
Patent number
US06297247B1

Reaction notes

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