Thiourea → HCID 86704191, compound

HRID 1497654Notes

Reaction equation

HRID 1497654 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH2:6][C:7]([C:9]1[C:10]([F:30])=[C:11]([N:15]([CH2:27][O:28][CH3:29])[S:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)=O>C(O)C>[NH2:1][C:2]1[S:3][CH:6]=[C:7]([C:9]2[C:10]([F:30])=[C:11]([N:15]([CH2:27][O:28][CH3:29])[S:16]([C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=3[F:26])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:4]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86704192HCID 86704192, compound

Product 1

HCID 86704191HCID 86704191, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

21 mg (0.27 mmol) of thiourea were added to a solution of 122 mg (0.27 mmol) of N-[3-(bromoacetyl)-2-fluorophenyl]-2,5-difluoro-N-(methoxymethyl)benzenesulfonamide in 5 mL of ethanol. The mixture was heated at 60° C. for 20 min in a microwave apparatus. The solvent was then removed, the residue taken up with DCM and washed with water. The organic layer was separated, dried over Na2SO4 and evaporated. The crude was purified by flash chromatography eluted with DCM-CH3OH 95/5, giving 92 mg (80%) of the title compound.

Workup

  1. customThe solvent was then removed
  2. washwashed with water
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe crude was purified by flash chromatography
  7. washeluted with DCM-CH3OH 95/5

Sources & evidence

ORD record
ord-11f452541fa24e51aeb76f5edfc84146
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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