Dimethylformamide → HCID 13173177, compound

HRID 980355Notes

Reaction equation

HRID 980355 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[C:11]([C:15]1[CH:16]=[C:17]([C:26]2[N:27]=[C:28]3[N:32]([CH:33]=2)[CH2:31][CH2:30][S:29]3)[CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[C:11]([C:15]1[CH:16]=[C:17]([C:26]2[N:27]=[C:28]3[N:32]([C:33]=2[CH:3]=[O:4])[CH2:31][CH2:30][S:29]3)[CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 13173170HCID 13173170, compound

Product 1

HCID 13173177HCID 13173177, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.5 ml of dimethylformamide in 10 ml of chloroform was added 1.1 g of phosphorus oxychloride under ice-cooling and the mixture was allowed to stand for one hour. To the reaction mixture was added 1.5 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole and the mixture was refluxed for 4 hours. To the reaction mixture was added 20 ml of an aqueous 10% potassium carbonate solution and the mixture was stirred for 15 minutes. The chloroform layer was dried and concentrated. The crystals thus obtained were recrystallized from ethanol to provide 1.0 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-formyl-2,3-dihydroimidazo[2,1-b]thiazole.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed for 4 hours
  3. dry with materialThe chloroform layer was dried
  4. concentrationconcentrated
  5. customThe crystals thus obtained
  6. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-29f56f2e1b904b809266141da4ad7b8c
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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