Diethylamine → N-(4-bromo-1,3-thiazol-5-yl)acetamide

HRID 1051417Notes

Reaction equation

HRID 1051417 reaction equation
Br[C:2]1[S:3][C:4]([NH:8][C:9](=[O:11])[CH3:10])=[C:5]([Br:7])[N:6]=1.C(NCC)C>C(O)C.[Ni]>[Br:7][C:5]1[N:6]=[CH:2][S:3][C:4]=1[NH:8][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 86715553N-(2,4-dibromothiazol-5-yl)acetamide

Product 1

HCID 83680500N-(4-bromo-1,3-thiazol-5-yl)acetamideYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(2,4-dibromothiazol-5-yl)acetamide from example 1.4 (0.35 g, 1.17 mmol), diethylamine (0.085 g, 1.17 mmol) and Raney Ni (0.14 g, 2.33 mmol) in ethanol (50 mL) was stirred at room temperature for 12 h in a 100 mL round-bottomed flask to give a black solution. The reaction mixture was filtered and concentrated to give the title compound (0.20 g, 0.91 mmol, 78%) as a yellow solid which was directly used for the next step without purification.

Workup

  1. customto give a black solution
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-20f70f9f594f4f83b1277f2452573fc9
Source dataset
uspto-grants-2016_07
Patent number
US09388180B2

Reaction notes

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