Phosgene → 1-chloro-N-(2-chloro-4-fluoro-5-isocyanatophenyl)methanesulfonamide

HRID 1107250

Reaction equation

HRID 1107250 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[C:7]([F:19])=[CH:8][C:9]([Cl:18])=[C:10]([NH:12][S:13]([CH2:16][Cl:17])(=[O:15])=[O:14])[CH:11]=1>C1(C)C=CC=CC=1>[Cl:17][CH2:16][S:13]([NH:12][C:10]1[CH:11]=[C:6]([N:5]=[C:1]=[O:2])[C:7]([F:19])=[CH:8][C:9]=1[Cl:18])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 11000212N-(5-amino-2-chloro4-fluorophenyl)-1-chloromethanesulfonamide

Product 1

HCID 110774021-chloro-N-(2-chloro-4-fluoro-5-isocyanatophenyl)methanesulfonamideYield 95.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of phosgene (68 mmol) in 35 mL toluene was added the title compound of Step D (4.2 g, 15.4 mmol) in 80 mL toluene at 0° C. and the reaction was stirred at room temperature overnight. The temperature was then raised to 70° C. for 4 h. After cooling to room temperature, the reaction mixture was filtrated and the solvent was removed under reduced pressure. Drying of the white precipitate under reduced pressure yielded the title compound of Step E (4.4 g, 95%) melting at 101.5-102.5° C. 1H NMR (CDCl3) δ 7.5 (d, 1H), 7.3 (d, 1H), 7.0-6.9 (br s, 1H), 4.64.5 (s, 2H).

Workup

  1. temperatureThe temperature was then raised to 70° C. for 4 h
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtrated
  4. customthe solvent was removed under reduced pressure
  5. customDrying of the white precipitate under reduced pressure

Sources & evidence

ORD record
ord-876da175843b498091fe36facd3e0ee5
Source dataset
uspto-grants-2000_05
Patent number
US06060432

Linked notes

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