Phosgene → [2-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamoyl Chloride

HRID 53241Notes

Reaction equation

HRID 53241 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:13])[O:4][N:3]=1.[C:14](Cl)([Cl:16])=[O:15]>ClCCl>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:13][C:14]([Cl:16])=[O:15])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 126766822-(3-Methyl-1,2,4-oxadiazol-5-yl)aniline

Product 1

HCID 19962135[2-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamoyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzenamine (1.0 g) in dry dichloromethane (20 ml) was added dropwise to a 0° solution of phosgene (14.1 ml, 20% in toluene) in dry dichloromethane (50 ml) under a nitrogen atmosphere. After addition the reaction mixture was allowed to slowly attain room temperature and stirred for 4 h. Nitrogen, was bubbled through the resulting mixture for 16 h. Dichloromethane was added to the resultant precipitate and the solution was evaporated to give the title compound (1.322 g), max (Nujol) 2800-2500, 1782 (NCO-Cl), 1631 (C=N), 1501 (NH), 769 (aromatic) cm-1.

Workup

  1. additionAfter addition the reaction mixture
  2. customwas allowed to slowly attain room temperature
  3. customNitrogen, was bubbled through the resulting mixture for 16 h
  4. additionDichloromethane was added to the resultant precipitate
  5. customthe solution was evaporated

Sources & evidence

ORD record
ord-3bb9fe0c9a7d418180e0999f8eff48f8
Source dataset
uspto-grants-1997_04
Patent number
US05618827

Reaction notes

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