N-bromobutanimide → 1239464-76-6

HRID 2098210Notes

Reaction equation

HRID 2098210 reaction equation
[S:1]1[C:5]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][N:3]=[CH:2]1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:14][C:4]1[N:3]=[CH:2][S:1][C:5]=1[NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53432624tert-Butyl 1,3-thiazol-5-ylcarbamate

Product 1

HCID 687870291239464-76-6

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl thiazol-5-ylcarbamate (WO 2007/071955) (607 mg, 3.0 mmol) in chloroform (50 mL) was added N-bromosuccinimide (542 mg, 3.04 mmol) at 0° C. After 1 h, reaction was quenched by addition of saturated NaHCO3 solution (50 mL). The layers were separated, and the mixture extracted with CHCl3 (3×50 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. 1H NMR (CDCl3) δ8.37 (d, J=0.6 Hz, 1H), 7.05 (br s, 1H), 1.55 (s, 9H); MH+ 278.9.

Workup

  1. customreaction
  2. customwas quenched by addition of saturated NaHCO3 solution (50 mL)
  3. customThe layers were separated
  4. extractionthe mixture extracted with CHCl3 (3×50 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82be265125a04e18af79a78c5dce16ed
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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