Water → N-(6-bromo-4-fluorobenzo[d]thiazol-2-yl)acetamide

HRID 2077531Notes

Reaction equation

HRID 2077531 reaction equation
[C:1]([NH:4][C:5]([NH:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([Br:15])=[CH:10][C:9]=1F)=[S:6])(=[O:3])[CH3:2].[H-].[Na+].O>CN(C=O)C>[Br:15][C:11]1[CH:12]=[C:13]([F:14])[C:8]2[N:7]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 575850341-Acetyl-3-(4-bromo-2,6-difluorophenyl)thiourea

Product 1

HCID 57585047N-(6-bromo-4-fluorobenzo[d]thiazol-2-yl)acetamideYield 102.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-acetyl-3-(4-bromo-2,6-difluorophenyl)thiourea (3.356 g, 10.86 mmol) was dissolved in DMF (100 ml) and the flask was cooled under nitrogen in an ice water bath. Then, sodium hydride (60% in mineral oil, 512.6 mg, 12.82 mmol) was added, and the reaction was warmed to room temperature and stirred for 1 hour. Then, the reaction flask was put in a preheated oil bath (130° C.) and stirred under nitrogen for an additional hour. The reaction was cooled to room temperature, poured into deionized water (300 ml), and filtered. The solid was washed with water and then dried by suction overnight to afford N-(6-bromo-4-fluorobenzo[d]thiazol-2-yl)acetamide (3.205 g, ˜100%). MS (ESI pos. ion) m/z: 289 (MH+, 79Br), 291 (MH+, 81Br). Calculated exact mass for C9H6BrFN2OS 288 (79Br), 290 (81Br).

Workup

  1. temperaturethe flask was cooled under nitrogen in an ice water bath
  2. customThen, the reaction flask was put in a preheated oil bath
  3. stirring(130° C.) and stirred under nitrogen for an additional hour
  4. temperatureThe reaction was cooled to room temperature
  5. filtrationfiltered
  6. washThe solid was washed with water
  7. customdried by suction overnight

Sources & evidence

ORD record
ord-f0056c5b92934443b6afb5119a462aaf
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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