4-Chlorophenyl Isocyanate → HCID 19417843, compound

HRID 865313Notes

Reaction equation

HRID 865313 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:4]=[C:5]([S:9]([NH2:12])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1>CC(C)=O>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:12][S:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:13])[CH3:1])[CH:4]=2)(=[O:11])=[O:10])=[O:25])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 140263423-(Dimethylamino)benzene-1-sulfonamide

Product 1

HCID 19417843HCID 19417843, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

The 3-(dimethylamino)benzenesulfonamide was dissolved in acetone (9.1 ml) to which was added 9.3 ml of 1N sodium hydroxide. To this mixture was added 4-chlorophenylisocyanate (1.43 g, 9.3 mmoles) dissolved in 9.1 ml of acetone. This mixture was stirred for 45 minutes at room temperature and then filtered. The filtrate was acidified using 1N hydrochloric acid (9.3 ml) and stirred for 2 hours, resulting in a precipitate. The solid was collected, washed thrice with water, and recrystallized using heated toluene (150 ml) and ethyl acetate (25 ml), followed by filtration and cooling.

Workup

  1. filtrationfiltered
  2. stirringstirred for 2 hours
  3. customresulting in a precipitate
  4. customThe solid was collected
  5. washwashed thrice with water
  6. customrecrystallized
  7. temperatureusing heated toluene (150 ml) and ethyl acetate (25 ml)
  8. filtrationfollowed by filtration
  9. temperaturecooling

Sources & evidence

ORD record
ord-45db4a7da912481a9d4e71336363d282
Source dataset
uspto-grants-1996_10
Patent number
US05565494

Reaction notes

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