Hydrochloric Acid → HCID 20344359, compound

HRID 2082906Notes

Reaction equation

HRID 2082906 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12].[OH-].[Na+].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>O>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([NH:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:10][C:11]([OH:13])=[O:12])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 5743497(2-(Aminomethyl)phenyl)acetic acid hydrochloride

Product 1

HCID 20344359HCID 20344359, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of o-aminomethylphenylacetic acid hydrochloride (7.50 g., 37 m.mol.) and sodium hydroxide (4.74 g., 118 m.mol.) in water (100 ml.) was added p-toluenesulfonyl chloride (7.64 g., 40 m.mol.) in portions at 60° C. The mixture was stirred for 1 hour at the same temperature and acidified with hydrochloric acid. The mixture was extracted with ethyl acetate (4 × 50 ml.). The combined extracts were washed with water, treated with a small amount of carbon and dried. The solvent was evaporated under reduced pressure and the residue crystallized from ethyl acetate to afford 2 as colorless prisms. Yield, 9.84 g. (84%). M.p. 155°-156° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (4 × 50 ml.)
  2. washThe combined extracts were washed with water
  3. additiontreated with a small amount of carbon
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-06295d35c12e4acb86788b34988724e3
Source dataset
uspto-grants-1978_04
Patent number
US04082912

Reaction notes

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