Dimethylformamide → HCID 21548311, compound

HRID 1605101Notes

Reaction equation

HRID 1605101 reaction equation
[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([OH:24])=[O:23])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].[C:30]([O:36][CH2:37]Cl)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32].CN(C)C=O>CCOCC>[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([O:24][CH2:37][O:36][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[O:23])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 87885Chloromethyl pivalateHCID 516893Potassium BicarbonateHCID 538804839-Benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid

Product 1

HCID 21548311HCID 21548311, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 12.8 g. of 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid, 20 g. of potassium bicarbonate, 12 ml. of chloromethyl pivalate in 50 ml. of dry dimethylformamide was stirred and heated on a steambath for two hours. The mixture was cooled and diluted with ether, the ether mixture was washed several times with water, dried over magnesium sulfate, and evaporated under reduced pressure to dryness to give 10.6 g. of the title compound; m.p. 75°-77°C. (methyl alcohol).

Workup

  1. additionA mixture of 12.8 g
  2. temperatureheated on a steambath for two hours
  3. temperatureThe mixture was cooled
  4. washthe ether mixture was washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure to dryness
  7. customto give 10.6 g

Sources & evidence

ORD record
ord-a3cb02ec519340de8e6b6e96eb1d1cdb
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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