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

HRID 2210326Notes

Reaction equation

HRID 2210326 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-bromoacetylthiazole 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-215bf7f683384eb69f34b746c3bfd950
Source dataset
uspto-grants-1995_10
Patent number
US05457205

Reaction notes

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