N-bromobutanimide → tert-butyl N-(5-bromo-1,3-thiazol-2-yl)carbamate

HRID 1521816Notes

Reaction equation

HRID 1521816 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[Br:14]N1C(=O)CCC1=O>C1COCC1>[Br:14][C:5]1[S:1][C:2]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11858898tert-butyl N-(1,3-thiazol-2-yl)carbamate

Product 1

HCID 21300388tert-butyl N-(5-bromo-1,3-thiazol-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 1,3-thiazol-2-ylcarbamate (90 g, 449.8 mmol, 1 eq.) is taken in THF (1.4 L) to which is added N-bromosuccinimide (88.06 g, 494.8 mmol, 1.1 eq.) portion wise. The reaction mixture is then stirred at RT overnight. The reaction mass is concentrated to remove THF. The crude is purified by column chromatography to get the titled produce. 1H NMR (DMSO-d6, 400 MHz): δ 11.73 (bs, 1H), 7.42 (s, 1H), 1.46 (s, 9H).

Workup

  1. concentrationThe reaction mass is concentrated
  2. customto remove THF
  3. customThe crude is purified by column chromatography
  4. customto get the
  5. customtitled produce

Sources & evidence

ORD record
ord-d343d4bc16264bdb910f072d62b7522d
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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