Dimethylformamide → HCID 21548377, compound

HRID 1605092Notes

Reaction equation

HRID 1605092 reaction equation
[H-].[Na+].CN(C)C=O.[CH2:8]1[C:20]2[NH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[CH:11]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:10][CH2:9]1.[C:31]1([CH3:40])[CH:36]=[CH:35][C:34]([C:37](Cl)=[O:38])=[CH:33][CH:32]=1>CCOCC.O.C(O)(=O)C>[C:31]1([CH3:40])[CH:36]=[CH:35][C:34]([C:37]([N:19]2[C:20]3[CH2:8][CH2:9][CH2:10][CH:11]([C:21]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[O:22])[C:12]=3[C:13]3[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:38])=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 6228Dimethylformamide3×HCID 134054-Methylbenzoyl ChlorideHCID 24758Sodium hydrideHCID 21548342HCID 21548342, compound

Product 1

HCID 21548377HCID 21548377, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a steam bath warmed mixture of 1.5 g sodium hydride in 25 ml. of dry dimethylformamide was added, dropwise and with stirring, 9.15 g. of benzyl 1,2,3,4-tetrahydrocarbazole-4-carboxylate in 25 ml. dry dimethylformamide followed by 5.4 g. of 4-toluoyl chloride in 15 ml. dry dimethylformamide, and heating was continued for two hours. The mixture was cooled and diluted with ether and 1.5 ml. glacial acetic acid. Water was added, the layers were separated and the ether extract was washed with water, 5% potassium bicarbonate solution, 1% aqueous hydrochloric acid and water, and dried over magnesium sulfate. The ether was evaporated to give the title compound which was used without purification in the next step.

Workup

  1. temperatureTo a steam bath warmed
  2. temperatureThe mixture was cooled
  3. customthe layers were separated
  4. extractionthe ether extract
  5. washwas washed with water, 5% potassium bicarbonate solution, 1% aqueous hydrochloric acid and water
  6. dry with materialdried over magnesium sulfate
  7. customThe ether was evaporated

Sources & evidence

ORD record
ord-0fc522fd6ed04136a0c09c3f674cfa61
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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