N-bromobutanimide → Ethyl 2-(bromomethyl)thiazole-5-carboxylate

HRID 1275881Notes

Reaction equation

HRID 1275881 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][CH:7]=1)=[O:5])[CH3:2].[Br:12]N1C(=O)CCC1=O>C(OCC)(=O)C>[Br:12][CH2:11][C:9]1[S:10][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12808791Ethyl 2-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 21840919Ethyl 2-(bromomethyl)thiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-5-thiazolecarboxylic acid ethyl ester (3.9 g) (J. Am. Chem. Soc. 1982, 104, 4461), N-bromosuccinimide (4.1 g) and catalytic azoisobutyronitrile in ethyl acetate (150 ml) was heated at reflux and under a 500 W halogen lamp for 16 hours. The solution was washed with water, dried (MgSO4) and evaporated. Purification was by chromatography eluting with 50% ethyl acetate in isohexane. Yield 1.5 g.

Workup

  1. washThe solution was washed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customPurification
  5. washeluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a7c83e01a09e42c2a564b80d2b2979fd
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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