Acetic Acid → tert-Butyl (5-bromo-4-cyclopropyl-1,3-thiazol-2-yl)carbamate

HRID 2109772Notes

Reaction equation

HRID 2109772 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[S:7][CH:8]=2)[CH2:3][CH2:2]1.C(#N)C.CC(O)=O.[Br:24]N1C(=O)CCC1=O>C([O-])(O)=O.[Na+]>[Br:24][C:8]1[S:7][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[N:5][C:4]=1[CH:1]1[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 57634179HCID 57634179, compound

Product 1

HCID 45117858tert-Butyl (5-bromo-4-cyclopropyl-1,3-thiazol-2-yl)carbamateYield 86.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a 250 mL round-bottomed flask was added tert-butyl 4-cyclopropylthiazol-2-ylcarbamate (9.5 g, 40 mmol), ACN 100% (100 mL, 1914 mmol), and glacial AcOH (6.8 mL, 119 mmol). The solution was stirred at 0° C. and treated in portions with N-bromosuccinimide (3.4 mL, 40 mmol). The suspension was stirred for 1 hour, diluted with NaHCO3, and extracted with EtOAc. The organics were washed with saturated sodium chloride (1×50 mL) and water (1×50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give tert-butyl 5-bromo-4-cyclopropylthiazol-2-ylcarbamate (11 g, 86% yield), m/z (%): 320.3 (100%, M++H).

Workup

  1. stirringThe suspension was stirred for 1 hour
  2. extractionextracted with EtOAc
  3. washThe organics were washed with saturated sodium chloride (1×50 mL) and water (1×50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dee9706ca5ec487798642b92c09ffc09
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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