Hydrochloric Acid → HCID 19037354, compound

HRID 263502Notes

Reaction equation

HRID 263502 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].Cl>[OH-].[Na+]>[C:25]1([CH2:24][O:23][C:21]([NH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH2:9][CH2:10][C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13]([OH:15])=[O:14])=[O:22])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 67719038HCID 67719038, compound

Product 1

HCID 19037354HCID 19037354, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

A suspension of 2-[2-(2-aminophenyl)ethyl]benzoic acid hydrochloride (339 mg, 1 mmol) in aqueous sodium hydroxide (1N, 2 mL) was stirred vigorously and treated simultaneously with benzyl chloroformate (170 mg, 1 mmol) and aqueous sodium hydroxide (1N, 1 mL). The reaction mixture was stirred for 16 h, acidified with dilute hydrochloric acid and filtered. The solid was washed with water and hexane, dissolved with methylene chloride, and the organic phase was washed with water, dried with magnesium sulfate, filtered and concentrated in vacuo. The resulting solid was triturated with ether to give 2-[2-(2-(phenylmethoxy-carbonylamino)phenyl)ethyl]benzoic acid (0.2 g, 53%).

Workup

  1. stirringThe reaction mixture was stirred for 16 h
  2. filtrationfiltered
  3. washThe solid was washed with water and hexane
  4. dissolutiondissolved with methylene chloride
  5. washthe organic phase was washed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting solid was triturated with ether

Sources & evidence

ORD record
ord-d4f0ceef18884d9cb758415a3ee0aa87
Source dataset
uspto-grants-1997_07
Patent number
US05643872

Reaction notes

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