Hydrochloric Acid → 2-Chloro-4-bromoacetyl-thiazole

HRID 477085Notes

Reaction equation

HRID 477085 reaction equation
N[C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:10])[CH2:8][Br:9])[N:6]=1.N([O-])=O.[Na+].[ClH:15]>O.[Cu]Cl>[Cl:15][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:10])[CH2:8][Br:9])[N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 136062401-(2-Aminothiazol-4-yl)-2-bromoethanoneHCID 23668193Sodium Nitrite

Product 1

HCID 143477622-Chloro-4-bromoacetyl-thiazole

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

7.6 g (6.0344 mol) of 2-Amino-4-bromoacetyl-thiazole are dissolved in 20 ml of water and 50 ml of concentrated hydrochloric acid. Now, at 0° C. and with stirring, a solution of 3.44 g (0.0499 mol) of sodium nitrite in 15 ml of water is added dropwise. The resulting diazonium salt solution is then introduced in portions into a vigorously stirred cold solution of 4.93 g (0.0449 mol) of copper(I) chloride in 15 ml of concentrated hydrochloric acid, and the mixture is stirred at room temperature for 20 hours. It is then diluted with 100 ml of water and extracted with ether. The ether extract is dried over sodium sulphate and evaporated. For purification, the crude product is purified on a silica gel column using methylene chloride as the eluant.

Workup

  1. stirringthe mixture is stirred at room temperature for 20 hours
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. dry with materialis dried over sodium sulphate
  5. customevaporated
  6. customFor purification
  7. customthe crude product is purified on a silica gel column

Sources & evidence

ORD record
ord-7b1c0788ed7149e6acf675abb5fc8665
Source dataset
uspto-grants-1989_12
Patent number
US04886814

Reaction notes

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