Water → 1-Acetyl-3-(4-bromo-2,6-difluorophenyl)thiourea

HRID 2077530Notes

Reaction equation

HRID 2077530 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH2:9])=[C:4]([F:10])[CH:3]=1.[C:11]([N:14]=[C:15]=[S:16])(=[O:13])[CH3:12].O>CC(C)=O>[C:11]([NH:14][C:15]([NH:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:10])=[S:16])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 128851Acetyl isothiocyanateHCID 6101914-Bromo-2,6-difluoroaniline

Product 1

HCID 575850341-Acetyl-3-(4-bromo-2,6-difluorophenyl)thioureaYield 91.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
72 °C

Procedure

4-bromo-2,6-difluorobenzenamine (2.514 g, 12.1 mmol) was dissolved in acetone (75 ml) and ethanoyl isothiocyanate (1.30 ml, 14.8 mmol) was added. The reaction flask was fit with a reflux condensor and placed in a preheated oil bath (70-74° C.) and the reaction was stirred under nitrogen for 90 minutes. The reaction was then cooled to room temperature and poured into water (200 ml), and the resultant suspension was filtered. The solid was washed with water, collected, and dried under high vacuum in water bath (60° C.) to afford 1-acetyl-3-(4-bromo-2,6-difluorophenyl)thiourea (3.435 g, 93% purity, 85% yield). MS (ESI pos. ion) m/z: 309 (MH+, 79Br), 311 (MH+, 81Br). Calculated exact mass for C9H7BrF2N2OS 308 (79Br), 310 (81Br).

Workup

  1. customplaced in a preheated oil bath
  2. temperatureThe reaction was then cooled to room temperature
  3. filtrationthe resultant suspension was filtered
  4. washThe solid was washed with water
  5. customcollected
  6. dry with materialdried under high vacuum in water bath (60° C.)

Sources & evidence

ORD record
ord-382a4375674c47e9878c0280051fd07a
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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