Chlorosuccinimide → HCID 21314424, compound

HRID 1679575Notes

Reaction equation

HRID 1679575 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:10]([NH:12][CH:13]1[C:30](=[O:31])[N:15]2[CH:16]([C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23])[C:17]([CH3:21])([CH3:20])[S:18](=[O:19])[C@H:14]12)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:38]N1C(=O)CCC1=O>>[CH3:20][C:17](=[CH2:21])[CH:16]([N:15]1[C:30](=[O:31])[CH:13]([NH:12][C:10](=[O:11])[CH:9]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:14]1[S:18]([Cl:38])=[O:19])[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23]

Participants

3

Reactant 2

HCID 31398ChlorosuccinimideHCID 86735570HCID 86735570, compound

Product 1

HCID 21314424HCID 21314424, compound

Procedure

A solution of 2.85 g. (5 mmol) of 2,2,2-trichloroethyl 6-(α-t-butyloxycarbonylaminophenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide in 175 ml. of toluene was dried azeotropically by distillation of about 50 ml. of toluene from the mixture. To the dried solution was added 0.685 g. (5.5 mmol.) of N-chlorosuccinimide. The resulting mixture was refluxed for 70 minutes. The mixture was allowed to cool to room temperature and then was filtered and evaporated in vacuo to dryness to provide the title product (contaminated with succinimide).

Workup

  1. dry with materialof toluene was dried azeotropically by distillation of about 50 ml
  2. additionTo the dried solution was added 0.685 g
  3. temperatureThe resulting mixture was refluxed for 70 minutes
  4. filtrationwas filtered
  5. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-98fc665d92974c7d8d6503b7e09413d9
Source dataset
uspto-grants-1978_03
Patent number
US04081440

Reaction notes

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