Dichloromethane → HCID 21332187, compound

HRID 1390952Notes

Reaction equation

HRID 1390952 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C(Cl)Cl.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]2[C:23]([Cl:24])=[C:22]([C:25]#[N:26])[S:21][C:20]=2[CH:27]=1>N1C=CC=CC=1>[C:2]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[C:23]([Cl:24])=[C:22]([C:25]#[N:26])[S:21][C:20]=2[CH:27]=1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 10387Benzyl chloroformateHCID 21332176HCID 21332176, compound

Product 1

HCID 21332187HCID 21332187, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 19.0 g. of benzyl chloroformate in 100 ml. of methylene chloride was added to a stirred solution of 0.1 mole of the amine in 500 ml. of methylene chloride containing 20 ml. of pyridine. The reaction mixture was stirred overnight at room temperature and then concentrated to dryness in vacuo. The solid residue was triturated with 5% hydrochloric acid solution and then recrystallized from ethanol to yield 6-carbobenzyloxyamino-3-chlorobenzo[b]thiophene-2-carbonitrile, m.p. 155°-166° C.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customThe solid residue was triturated with 5% hydrochloric acid solution
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-731692dafbab4eb8b62b4f0923a5594e
Source dataset
uspto-grants-1979_02
Patent number
US04140785

Reaction notes

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