Ammonia → 4-Thiazolemethanol, alpha-(bromomethyl)-2-(trifluoromethyl)-

HRID 477086Notes

Reaction equation

HRID 477086 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[S:4][CH:5]=[C:6]([C:8](=[O:11])[CH2:9][Br:10])[N:7]=1.[BH4-].[Na+].Cl.N>CO>[F:13][C:2]([F:1])([F:12])[C:3]1[S:4][CH:5]=[C:6]([CH:8]([OH:11])[CH2:9][Br:10])[N:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10978660HCID 10978660, compound

Product 1

HCID 222204994-Thiazolemethanol, alpha-(bromomethyl)-2-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

6 g (0.022 mol) of 2-Trifluoromethyl-4-bromoacetyl-thiazole are dissolved in 150 ml of methanol, and the solution is cooled to 10° C. and 0.63 g of sodium borohydride is added. After 15 minutes ice is added, and the mixture is acidified with hydrochloric acid, made alkaline with ammonia and extracted by shaking with methylene chloride. The organic phase is dried over sodium sulphate, filtered and concentrated. An oil is obtained and is reacted further as the crude product.

Workup

  1. additionAfter 15 minutes ice is added
  2. extractionextracted
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customAn oil is obtained

Sources & evidence

ORD record
ord-3a54d529ba3746babc35a3b2bbf99975
Source dataset
uspto-grants-1989_12
Patent number
US04886814

Reaction notes

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