Water → N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide

HRID 1107249Notes

Reaction equation

HRID 1107249 reaction equation
[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.[Cl:14][CH2:15][S:16](Cl)(=[O:18])=[O:17].O>N1C=CC=CC=1>[Cl:13][C:3]1[C:2]([NH:1][S:16]([CH2:15][Cl:14])(=[O:18])=[O:17])=[CH:7][C:6]([NH:8][C:9](=[O:11])[CH3:10])=[C:5]([F:12])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77054(Chloromethyl)sulfonyl chloride2×HCID 11769584N-(5-amino-4-chloro-2-fluorophenyl)acetamide

Product 1

HCID 10870764N-[4-chloro-5-[[(chloromethyl)sulfonyl]amino]-2-fluorophenyl]acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of the title compound of Step B (8.10 g, 40 mmol) in pyridine (50 mL) was added chloromethylsulfonyl chloride (3.84 mL, 40.45 mmol) over 30 minutes at 0° C. After stirring at room temperature for 14 h, chloromethylsulfonyl chloride (0.38 mL, 4.05 mmol) was added to complete the reaction. Water was added so that the product precipitated. After filtration and washing with water and petroleum ether, the title compound of Step C was isolated as a bright powder (11.17 g, 89%) melting at 208-210° C. 1H NMR (Me2SO-d6) δ 10.2-10.1 (s, 1H), 9.9 (s, 1H), 8.1 (d, 1H), 7.6-7.5 (d, 1H), 5.0-4.9 (s, 2H), 2.1 (s, 3H).

Workup

  1. customthe reaction
  2. customprecipitated
  3. filtrationAfter filtration
  4. washwashing with water and petroleum ether

Sources & evidence

ORD record
ord-6fd0768f482c4454bc4dcd8c04041dc1
Source dataset
uspto-grants-2000_05
Patent number
US06060432

Reaction notes

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