Sulfanilamide → HCID 67484576, compound

HRID 1814636Notes

Reaction equation

HRID 1814636 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)[CH:16]([CH3:18])[CH3:17])(C)C.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23].Cl[CH2:32]Cl>>[C:25]1([O:24][C:22](=[O:23])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:9])(=[O:10])[NH:11][CH2:32][CH2:18][CH2:16][CH3:17])=[CH:4][CH:3]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 5333SulfanilamideHCID 6344Dichloromethane2×HCID 15891Phenyl chloroformateHCID 81531Diisopropylethylamine

Product 1

HCID 67484576HCID 67484576, compound

Procedure

The above 4-aminophenylsulfonamide (0.14 g) was dissolved in dichloromethane (6 mL), N,N-diisopropylethylamine (172 μL, 1 mmol) and phenyl chloroformate (122 μL, 0.92 mmol) and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with dichloromethane (50 mL) and was washed with 1N hydrochloric acid (3×20 mL), water (3×20 mL), a mixture of water and a saturated solution of sodium hydrogen carbonate (1:1, 2×20 mL) and a mixture of water and a saturated solution of sodium chloride (1:1, 2×20 mL). Drying (MgSO4) and concentration in vacuo afforded crude (4-butylsulfamoylphenyl)carbamic acid phenyl ester.

Workup

  1. washwas washed with 1N hydrochloric acid (3×20 mL), water (3×20 mL)
  2. additiona mixture of water
  3. additiona saturated solution of sodium hydrogen carbonate (1:1, 2×20 mL) and a mixture of water
  4. customDrying
  5. concentration(MgSO4) and concentration in vacuo

Sources & evidence

ORD record
ord-c6aeaa84c3c24ad08e73f38f884567e1
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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