Water → HCID 86245203, compound

HRID 2262959Notes

Reaction equation

HRID 2262959 reaction equation
[NH2:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([Cl:11])=[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].O>O1CCCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([NH:1][C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[N:6][C:5]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 61035-Chloro-2-benzoxazolamineHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 86245203HCID 86245203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-chlorobenzoxazole (1.00 g, 5.39 mmol) and pyridine (0.564 ml, 7.12 mmol) in tetrahydrofuran (20 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (0.850 ml, 7.12 mmol), and the mixture was stirred at room temperature for 2 hours and half. Water was poured to the reaction mixture, and the resulting solution 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. Hexane was poured to the residue, and 394 mg (19.3%) of the desired product as a solid was separated by filtration.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was poured to the residue, and 394 mg (19.3%) of the desired product as a solid
  7. customwas separated by filtration

Sources & evidence

ORD record
ord-d249ddfe7607447590ef70a5d7c4d9aa
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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