Phenylmethanesulfonyl chloride → HCID 18926408, compound

HRID 1600070Notes

Reaction equation

HRID 1600070 reaction equation
[CH2:1]([S:8](Cl)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[C:14](=[O:26])[N:15]([CH2:23][CH:24]=[CH2:25])[C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1>N1C=CC=CC=1>[CH2:1]([S:8]([NH:12][C:13]1[C:14](=[O:26])[N:15]([CH2:23][CH:24]=[CH2:25])[C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 18926409HCID 18926409, compound

Product 1

HCID 18926408HCID 18926408, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzylsulfonyl chloride (103 mg, 0.542 mmol) was added to a stirred solution of 3-amino-6-trifluoromethyl-1-allyl-2-pyridinone (106.5 mg, 0.488 mmol) in pyridine (1 ml) at 0° C. After 1 h the reaction was evaporated in vacuo and the residue was partitioned between methylene chloride and 10% potassium hydrogen sulfate solution, dried (Na2 SO4), and evaporated in vacuo to give the title compound (175.8 mg): 1H NMR (CDCl3) selected signals at δ4.42 (s, 2H), 4.74 (d, J=5.5 Hz, 2H), 5.16-5.31 (m, 2H), 5.86-5.96 (m, 1H), 6.55 (d, J=7.7 Hz, 1H), 7.11 (d, J=7.9 Hz, 1H), 7.27-7.33 (m, 5H), 7.70 (br s, 1H, NH).

Workup

  1. customAfter 1 h the reaction was evaporated in vacuo
  2. customthe residue was partitioned between methylene chloride and 10% potassium hydrogen sulfate solution
  3. customdried (Na2 SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ec3cc74ccf4d4c64acca8f72f607b13c
Source dataset
uspto-grants-1998_04
Patent number
US05744486

Reaction notes

Loading…