Phenyl isocyanate → HCID 21184658, compound

HRID 323027Notes

Reaction equation

HRID 323027 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:5]=1)([O-:3])=[O:2].[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:28]([NH:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:29])=[C:6]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7672Phenyl isocyanateHCID 13109537HCID 13109537, compound

Product 1

HCID 21184658HCID 21184658, compound

Procedure

N-(4-Nitro 2-(phenylsulfonylamino)phenyl)-N′-phenyl urea was prepared from 4-nitro 2-(phenylsulfonylamino) aniline (82 mg) and phenyl isocyanate (33 mg) by method A. The reaction was cooled and then partitioned between saturated ammonium chloride and 9:1 methylene chloride and methanol. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/hexanes) to afford desired (30.8 mg, 26%). EI-MS m/z 413 (M+H)+

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between saturated ammonium chloride and 9:1 methylene chloride and methanol
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (ethyl acetate/hexanes)
  7. customto afford

Sources & evidence

ORD record
ord-4978d61e77cc46fd8305551d9ca11b64
Source dataset
uspto-grants-2001_04
Patent number
US06211373B1

Reaction notes

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