Chlorosulfonyl isocyanate → HCID 90055122, compound

HRID 1772928Notes

Reaction equation

HRID 1772928 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[F:8][C:9]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:10]=1[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](CC)([O-])=O>[F:8][C:9]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[C:10]=1[CH2:11][N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:2](=[O:4])(=[O:3])[NH:5][C:6]1=[O:7]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanateHCID 6451240Aluminum(III) ChlorideHCID 65098528HCID 65098528, compound

Product 1

HCID 90055122HCID 90055122, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of chlorosulfonylisocyanate (4.72 mL, 54.2 mmol) in nitroethane (75 mL) was cooled to approximately −40° C. and a solution of N-(2,4,6-trifluorobenzyl)aniline (9.90 g, 41.7 mmol) in nitroethane (75 mL) added dropwise over approximately 10 min. The mixture was stirred at −40° C. for 10 min, then at 0° C. for 30 min. Aluminium chloride (5.56 g, 41.7 mmol) was added and the mixture heated at reflux for 30 min, before cooling to rt and cautious addition to stirred ice-H2O (approximately 250 mL). The title compound (6.12 g, 17.9 mmol) was isolated by filtration.

Workup

  1. waitat 0° C. for 30 min
  2. temperaturethe mixture heated
  3. temperatureat reflux for 30 min
  4. temperaturebefore cooling to rt
  5. additioncautious addition

Sources & evidence

ORD record
ord-cfffcd39e3c746bf8ac08f403efff4b4
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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