Benzene → HCID 21831352, compound

HRID 363475Notes

Reaction equation

HRID 363475 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 bromoacetoaldehyde 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-0e6918845c9346859fef1e1103b03458
Source dataset
uspto-grants-1999_02
Patent number
US05874446

Reaction notes

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