Benzoyl chloride → HCID 12802317, compound

HRID 223302Notes

Reaction equation

HRID 223302 reaction equation
[C:1]1([NH:7][C:8]2[C:13](=[O:14])[NH:12][C:10](=[O:11])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CC(C)=O>[C:1]1([NH:7][C:8]2[C:13](=[O:14])[N:12]([C:15](=[O:22])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10](=[O:11])[CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11819805HCID 11819805, compound

Product 1

HCID 12802317HCID 12802317, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.88 g. (0.01 mole) of 3-phenylamino-maleinimide are dissolved in 70 ml. of acetone under stirring. To this mixture 2.1 g. (0.015 mole) of benzoyl chloride and 1.51 g. (0.015 mole) of triethylamine are added dropwise under simultaneous stirring. The temperature is maintained at 25°-30° C. during the addition. The mixture is then stirred for 2.5 hours at room temperature and heated for 1.5 hours. The mixture is allowed to stand overnight. The product is precipitating together with triethylaminechlorohydrate. The crystalline mixture is filtered and washed with 2×10 ml. of water. After drying a yellow crystalline product is obtained, which can be recrystallized from chloroform or acetone, if desired. 3-Phenylamino-N-benzoyl-maleinimide is obtained.

Workup

  1. temperatureThe temperature is maintained at 25°-30° C. during the addition
  2. temperatureheated for 1.5 hours
  3. waitto stand overnight
  4. customThe product is precipitating together with triethylaminechlorohydrate
  5. filtrationThe crystalline mixture is filtered
  6. washwashed with 2×10 ml
  7. customAfter drying a yellow crystalline product
  8. customis obtained
  9. customwhich can be recrystallized from chloroform or acetone

Sources & evidence

ORD record
ord-4648c6f7500a4c7b9b9966c8eb97e7bd
Source dataset
uspto-grants-1982_10
Patent number
US04353734

Reaction notes

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