Chlorosulfonyl isocyanate → HCID 90055181, compound

HRID 1772926Notes

Reaction equation

HRID 1772926 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[F:8][C:9]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[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]=[CH:21][CH:20]=[C:19]([F:23])[C:10]=1[CH2:11][N:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[S:2](=[O:4])(=[O:3])[NH:5][C:6]1=[O:7]

Participants

5

Reactant 3

HCID 70918Chlorosulfonyl isocyanate2×HCID 6451240Aluminum(III) Chloride2×HCID 28424096HCID 28424096, compound2×

Product 1

HCID 90055181HCID 90055181, compoundYield 366%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent4×

Conditions

Temperature
-40 °C

Procedure

A solution of chlorosulfonylisocyanate (0.29 mL, 3.33 mmol) in nitroethane (5 mL) was cooled to approximately −40° C. and a solution of N-(2,6-difluorobenzyl)aniline (562 mg, 2.56 mmol) in nitroethane (3 mL) was added dropwise over approximately 10 min. The mixture was stirred at −40° C. for approximately 10 min, then at 0° for 15 min. Aluminium chloride (479 mg, 3.59 mmol) was then added and the mixture heated at reflux for 30 min before cooling to rt. Separately, the process was repeated using chlorosulfonylisocyanate (1.20 mL, 13.8 mmol) in nitroethane (20 mL), N-(2,6-difluorobenzyl)aniline (2.32 g, 10.6 mmol) in nitroethane (15 mL), followed by aluminium chloride (1.97 g, 14.8 mmol). The two reaction mixtures were combined and cautiously added to stirred ice-H2O (approximately 100 mL) and the title compound (3.04 g, 9.37 mmol) was isolated by filtration.

Workup

  1. waitat 0° for 15 min
  2. temperaturethe mixture heated
  3. temperatureat reflux for 30 min
  4. temperaturebefore cooling to rt
  5. customThe two reaction mixtures
  6. additioncautiously added

Sources & evidence

ORD record
ord-0d7e37f789904eaf8dee5af76dfda0bc
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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