4-Nitrobenzenesulfonamide → 1-(4'-Nitrobenzenesulfonyl)-3-methoxycarbonyl urea

HRID 2106914Notes

Reaction equation

HRID 2106914 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][O:15][C:16]([N:18]=[C:19]=[O:20])=[O:17]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:19]([NH:18][C:16]([O:15][CH3:14])=[O:17])=[O:20])(=[O:11])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 227844-NitrobenzenesulfonamideHCID 4156749Methyl isocyanatoformate

Product 1

HCID 230496241-(4'-Nitrobenzenesulfonyl)-3-methoxycarbonyl ureaYield 79.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 1140TolueneSolvent

Procedure

To 4-nitrobenzenesulfonamide (2.1 grams, 0.01 mole) in 100 milliliters dry toluene was added 1.2 grams (0.012 mole) methoxycarbonyl isocyanate. Three drops of pyridine were added. The mixture was refluxed for four hours. After cooling the precipitate was filtered off and washed with toluene. The solid material was dried. There was obtained 2.4 grams of the title compound, m.p. 150°-158° C.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. temperatureAfter cooling the precipitate
  3. filtrationwas filtered off
  4. washwashed with toluene
  5. customThe solid material was dried

Sources & evidence

ORD record
ord-bc220545435a4a8ba84aa91d0580c284
Source dataset
uspto-grants-1990_06
Patent number
US04931580

Reaction notes

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