Maleic Anhydride → N-(4-Azidosulfonylphenyl)-maleic acid monoamide

HRID 1065586Notes

Reaction equation

HRID 1065586 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]=[N+:19]=[N-:20])(=[O:17])=[O:16])=[CH:11][CH:10]=1>ClCCl>[N:18]([S:15]([C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])=[CH:14][CH:13]=1)(=[O:16])=[O:17])=[N+:19]=[N-:20]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 112064084-Aminobenzenesulfonyl azide2×

Product 1

HCID 11197210N-(4-Azidosulfonylphenyl)-maleic acid monoamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

100 g maleic acid anhydride are dissolved in 1 liter dichloromethane and to this solution are added drop-wise 198 g of the 4-aminobenzenesulfonylazide (approximately 1 mol) prepared according to (3), dissolved in 400 ml dichloromethane. The reaction mixture is left standing for 2 hours at room temperature. The solution is then concentrated in a rotary evaporator to about 200 ml. The light brown product obtained is cooled, filtered, washed with a small amount of dichloromethane and finally dried.

Workup

  1. customprepared
  2. waitThe reaction mixture is left
  3. concentrationThe solution is then concentrated in a rotary evaporator to about 200 ml
  4. customThe light brown product obtained
  5. temperatureis cooled
  6. filtrationfiltered
  7. washwashed with a small amount of dichloromethane
  8. customfinally dried

Sources & evidence

ORD record
ord-e0fe462fc2674dc19db97d5c3b9778e6
Source dataset
uspto-grants-1982_05
Patent number
US04329556

Reaction notes

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