Dimethylformamide → HCID 46880047, compound

HRID 596923Notes

Reaction equation

HRID 596923 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:16])[O:10][CH2:11][C:12]#CCO)[CH:5]=[CH:6][CH:7]=1.CN(C)C=O.C(Cl)([Cl:24])=O>C(Cl)CCl.C1C=CC=CC=1>[CH:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([NH:8][C:9]([O:10][C:11]#[C:12][Cl:24])=[O:16])[CH:5]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6371PhosgeneHCID 766204-Hydroxy-2-butynyl (3-chlorophenyl)carbamate

Product 1

HCID 46880047HCID 46880047, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 241BenzeneSolvent

Procedure

To a warm (50°) stirred solution of 4-hydroxy-2-butynyl N-(3-chlorophenyl)carbamate (59.9 g., 0.500 mole) and dimethylformamide (0.6 g) in 150 ml of EDC was added 250 ml of 12.5% phosgene in benzene over a period of about 30 minutes. The reaction mixture was heated at 50° for 4.5 more hours, then at 60° for 2 hours. Evaporation of solvent afforded a quantitative yield of technical barban.

Workup

  1. temperatureTo a warm (50°)
  2. temperatureThe reaction mixture was heated at 50° for 4.5 more hours
  3. customEvaporation of solvent

Sources & evidence

ORD record
ord-9da1a33fbd1643b29801ea2c214927f1
Source dataset
uspto-grants-1977_03
Patent number
US04012433

Reaction notes

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