Pyridine → 2,2,2-Trichloroethyl (2-methyl-1,3-benzoxazol-6-yl)carbamate

HRID 2263228Notes

Reaction equation

HRID 2263228 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20]>CN(C)C(=O)C>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([NH:11][C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 5905392-Methyl-1,3-benzoxazol-6-amine

Product 1

HCID 862451832,2,2-Trichloroethyl (2-methyl-1,3-benzoxazol-6-yl)carbamate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-methyl-1,3-benzoxazol-6-amine (1.00 g, 6.74 mmol) and pyridine (1.64 ml, 20.2 mmol) in N,N-dimethylacetamide (20 ml) was added 2,2,2-trichloroethyl chloroformate (1.39 ml, 10.1 mmol) under ice-cooling, and the mixture was stirred for 2 hours under ice-cooling. The reaction mixture was poured into ice-water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and ethyl acetate, and 1.45 g (66.5%) of the desired product was collected by filtration as a solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from a mixed solvent of hexane and ethyl acetate, and 1.45 g (66.5%) of the desired product
  8. filtrationwas collected by filtration as a solid

Sources & evidence

ORD record
ord-3253433246ce4cf8a8aa3b945739d634
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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