Water → HCID 25208823, compound

HRID 1993804Notes

Reaction equation

HRID 1993804 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([Br:7])[N:6]=1.[Li+].CC([N-]C(C)C)C.[CH2:16]([N:23]=[C:24]=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C1COCC1>[CH2:16]([NH:23][C:24]([C:4]1[S:3][C:2]([Br:1])=[N:6][C:5]=1[Br:7])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 76639Benzyl isocyanateHCID 2724682Lithium diisopropylamideHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 25208823HCID 25208823, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 2,4-dibromo-thiazole (4.95 g, 20.4 mmol) in THF at −78° C. was added LDA (1.8M in THF/hexanes, 13.6 ml, 24.5 mmol) slowly. The reaction was then stirred at −78° C. for 30 min., when benzylisocyanate (3.8 ml, 30.6 mmol) was added slowly. The mixture was then stirred at −78° C. for 30 min. before it was slowly warmed up to RT. Water was then added carefully to quench the reaction. The mixture was extracted with EtOAc and the combined extracts were dried over sodium sulfate and concentrated. The crude product was purified by column chromatography on silica gel (10% EtOAc/hexanes) to give 2,4-dibromo-thiazole-5-carboxylic acid benzylamide 26B as a white solid (5.05 g, 13.43 mmol, 66%).

Workup

  1. stirringThe mixture was then stirred at −78° C. for 30 min. before it
  2. temperaturewas slowly warmed up to RT
  3. customto quench
  4. customthe reaction
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe combined extracts were dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography on silica gel (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6c2707eea3b8422db56caa1249f21e83
Source dataset
uspto-grants-2010_01
Patent number
US07652044B2

Reaction notes

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