Benzene → 5-Imidizolidinone, 1-(o-chloro-p-sulfamoylphenyl)-3-phenyl-

HRID 1658219Notes

Reaction equation

HRID 1658219 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:14][C:13]=2[Cl:22])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[CH:25]1C=CC=CC=1.CO>CN(C)C=O.O>[C:1]1([N:7]2[CH2:8][C:9](=[O:10])[N:11]([C:12]3[CH:17]=[CH:16][C:15]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:14][C:13]=3[Cl:22])[CH2:25]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 712FormaldehydeHCID 887MethanolHCID 21528839HCID 21528839, compound

Product 1

HCID 407115-Imidizolidinone, 1-(o-chloro-p-sulfamoylphenyl)-3-phenyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Phenylamino-N-(2-chloro-4-sulphamoylphenyl)-acetamide (0.8g) was dissolved in dimethylformamide (20ml) and paraformaldehyde (100 g) in water (5 ml) added thereto. The mixture was kept at 80° for 24 hours and then the DMF was evaporated. The residue was recrystallised from ethanol to yield the product (500 mg.), m.p. 204°; mixed melting point with the product of Example 3(c) 206°. The product was found identical with the product of Example 3(c) on thin layer chromatography (Kieselgel F254, Merck; benzene; methanol 16:1) and on IR spectroscopy.

Workup

  1. customthe DMF was evaporated
  2. customThe residue was recrystallised from ethanol
  3. customto yield the product (500 mg.), m.p. 204°

Sources & evidence

ORD record
ord-a0f7ef91b2144bd598daf719bbf849cd
Source dataset
uspto-grants-1976_06
Patent number
US03963706

Reaction notes

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