Benzoyl chloride → HCID 20501035, compound

HRID 851770Notes

Reaction equation

HRID 851770 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]2([C:27](=[O:28])[NH:26][C:25](=[O:29])[NH:24]2)[C:16]1=[O:30].C(N(CC)CC)C>COCCOC.C1(C)C=CC=CC=1>[C:1]([N:24]1[C:17]2([C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([CH2:14][C:13]3[CH:31]=[CH:32][C:33]([Cl:34])=[C:11]([Cl:10])[CH:12]=3)[C:16]2=[O:30])[C:27](=[O:28])[NH:26][C:25]1=[O:29])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 13564624HCID 13564624, compound

Product 1

HCID 20501035HCID 20501035, compoundYield 15.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of benzoyl chloride (0.63 g.) in 1,2-dimethoxyethane (10 ml.) was added dropwise to a stirred mixture of 1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (1.8 g.) and triethylamine (0.51 g.) in 1,2-dimethoxyethane (50 ml.) cooled at 0°-5° C. When the addition was completed, the solution was stirred at 20°-25° C. for three hours. Silica gel (5 g., Merck type 7734) was added to the solution and the mixture was evaporated The residue obtained was added to the top of a column of silica gel (75 g., Merck type 7734) made up in toluene. The column was eluted with increasing concentration of ethyl acetate in toluene up to 25% v/v and the fractions containing the major product [Relative flow value: 0.4, on Merck SiO2TLC plates No. 5715; eluant: EtOAc/Toluene, 1:1 v/v] were collected, combined and evaporated. The solid thereby obtained was recrystallised from ethyl acetate/petrol 60-80 to give 3-benzoyl-1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (0.34 g.), m.p. 251°-253° C.

Workup

  1. temperaturecooled at 0°-5° C
  2. additionWhen the addition
  3. additionSilica gel (5 g., Merck type 7734) was added to the solution
  4. customthe mixture was evaporated The residue
  5. customobtained
  6. additionwas added to the top of a column of silica gel (75 g., Merck type 7734)
  7. washThe column was eluted
  8. temperaturewith increasing concentration of ethyl acetate in toluene up to 25% v/v
  9. additionthe fractions containing the major product [Relative flow value
  10. customeluant: EtOAc/Toluene, 1:1 v/v] were collected
  11. customevaporated
  12. customThe solid thereby obtained
  13. customwas recrystallised from ethyl acetate/petrol 60-80

Sources & evidence

ORD record
ord-294744d0b5d746d29db085c160f5396b
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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