Chlorosulfonyl isocyanate → HCID 90054686, compound

HRID 1772923Notes

Reaction equation

HRID 1772923 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[Cl: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>[Cl: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) ChlorideHCID 137828892-Chloro-6-fluoro-N-phenylbenzenemethanamine

Product 1

HCID 90054686HCID 90054686, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of chlorosulfonylisocyanate (5.04 mL, 57.9 mmol) in nitroethane (100 mL) was cooled to approximately −40° C. and a solution of N-(2-chloro-6-fluorobenzyl)aniline (10.5 g, 44.6 mmol) in nitroethane (80 mL) added dropwise over approximately 10 min. The mixture was stirred at −40° C. for 10 min, then rt for 1 h, before the addition of further chlorosulfonylisocyanate (1.94 mL, 22.3 mmol) and stirring for 30 min at rt. Aluminium chloride (8.32 g, 62.4 mmol) was added and the mixture heated at reflux for 30 min, before cooling to rt and cautious addition to stirred ice-H2O (approximately 300 mL). After stirring for 15 min, the title compound (11.8 g, 34.6 mmol) was isolated by filtration.

Workup

  1. waitrt for 1 h
  2. stirringstirring for 30 min at rt
  3. temperaturethe mixture heated
  4. temperatureat reflux for 30 min
  5. temperaturebefore cooling to rt
  6. additioncautious addition
  7. stirringAfter stirring for 15 min

Sources & evidence

ORD record
ord-627d80ad3e4e496d805867e7042b7955
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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