Benzene → HCID 21831352, compound

HRID 1601415Notes

Reaction equation

HRID 1601415 reaction equation
[F:1][CH2:2][C:3]1([CH2:19][F:20])[CH:8]=[C:7]([C:9](=[S:11])[NH2:10])[C:6]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:5]=2[O:4]1.CO[CH:23](OC)[CH2:24]Br.[OH-].[K+].C1C=CC=CC=1>O>[F:20][CH2:19][C:3]1([CH2:2][F:1])[CH:8]=[C:7]([C:9]2[S:11][CH:23]=[CH:24][N:10]=2)[C:6]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:5]=2[O:4]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 14797Potassium HydroxideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 21831295HCID 21831295, compound

Product 1

HCID 21831352HCID 21831352, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 600 mg of 2,2-bisfluoromethyl-6-nitro-2H-1-benzopyran-4-carbothioamide, 1.2 ml of bromo-acetoaldehyde dimethylacetal, 11 mg of potassium hydroxide and 3 ml of benzene was refluxed with heating for 1 hour. Water was added thereto and the mixture was extracted with methylene chloride. The organic layer was washed with water and dried. The solvent was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, hexane:ethyl acetate=2:1) to obtain 380 mg of 2-(2,2-bisfluoromethyl-6-nitro-2H-1-benzopyran-4-yl)thiazol represented by the following formula.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 1 hour
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe resultant residue was purified

Sources & evidence

ORD record
ord-14d845606a754293be8076bc071b7aff
Source dataset
uspto-grants-1999_11
Patent number
US05977167

Reaction notes

Loading…