4-Chlorophenyl Isocyanate → HCID 19417852, compound

HRID 865312Notes

Reaction equation

HRID 865312 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2].[OH-].[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1>CC(C)=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([N:3]([CH2:1][CH3:2])[CH2:14][CH3:15])=[CH:9][CH:8]=2)(=[O:11])=[O:12])=[O:27])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 19417846HCID 19417846, compound

Product 1

HCID 19417852HCID 19417852, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

This benzenesulfonamide (0.99 g, 4.3 mmoles) was dissolved in acetone (4.3 ml) to which was then added 1.0N sodium hydroxide (4.4 ml). To this mixture was added 4-chlorophenylisocyanate (0.68 g, 4.4 mmoles), dissolved in 4.3 ml of acetone. This mixture was allowed to stir at room temperature for about 15 minutes. A solid was then removed from the reaction mixture by filtration. To the filtrate was added 1.0N hydrochloric acid (4.4 ml), causing separation of a brown oil. Water (5 ml) was then added and the mixture stirred until the oil had converted to a solid. The solid was collected and washed three times with water.

Workup

  1. customA solid was then removed from the reaction mixture by filtration
  2. additionTo the filtrate was added 1.0N hydrochloric acid (4.4 ml)
  3. customseparation of a brown oil
  4. additionWater (5 ml) was then added
  5. stirringthe mixture stirred until the oil
  6. customThe solid was collected
  7. washwashed three times with water

Sources & evidence

ORD record
ord-e6739d31ee624a619137aaea8ffc1bad
Source dataset
uspto-grants-1996_10
Patent number
US05565494

Reaction notes

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