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

HRID 1934832

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>C(C(C)=O)C(C)C>[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

Conditions

Temperature: 35 °C

Procedure

To a stirred solution of 218 g (2.2 mole) of phosgene in 0.6 L of methyl isobutyl ketone at 0° C. was added 546.2 g (2 mol) of N-(5-amino-2-chloro-4-fluorophenyl)-1-chloromethanesulfonamide dissolved in 2 L of methyl isobutyl ketone. During the addition (75 minutes) the temperature was kept between −3° C. and 3° C. The temperature of the solution was raised to 35° C. and 1 L of the solvent was distilled off under reduced pressure (11.0-11.5 kPa (110-115 mbar), maximum temperature: 60° C.). This isocyanate solution was used in the next step without further purification.

Workup

additionDuring the addition (75 minutes) the temperature
customwas kept between −3° C. and 3° C
distillation1 L of the solvent was distilled off under reduced pressure (11.0-11.5 kPa (110-115 mbar), maximum temperature: 60° C.)
customThis isocyanate solution was used in the next step without further purification

Sources & evidence

ORD record: ord-8a57f33a352d4bf99574f50b489ed1fb
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384234B1

Linked notes

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