4-Chlorobenzoyl chloride → HCID 53958540, compound

HRID 436510Notes

Reaction equation

HRID 436510 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[NH:9][C:8]=2[CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>CN(C)C=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[N:9]([C:27](=[O:28])[C:26]3[CH:30]=[CH:31][C:23]([Cl:22])=[CH:24][CH:25]=3)[C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 24758Sodium hydrideHCID 54455743HCID 54455743, compound

Product 1

HCID 53958540HCID 53958540, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 5.5 g. of 6-chloro-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid ethyl ester in 40 ml. of dimethylformamide was added 0.9 g. of 54.5 percent sodium hydride in mineral oil. After the mixture had stirred 1 hour at room temperature, 3.5 g. of p-chlorobenzoyl chloride in 10 ml. of dimethylformamide was added dropwise over the course of 10 minutes. The mixture was then stirred for 5 hours between 60°-70° and then poured onto ice (500 g.). The mixture was extracted with ether (3 × 150 ml.) and the ether was in turn extracted with water (5 × 100 ml.). After drying the ether solution over sodium sulfate, the desiccant was removed by filtration and the ether was evaporated. Upon recrystallization of the residue with ethyl acetate, 3.8 g. of product was obtained, m.p. 129°-132° . Following two further recrystallizations from methanol, a yield of 2.3 g. of 6-chloro-9-(p-chlorobenzoyl)-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid ethyl ester was obtained, m.p. 136°-137°.

Workup

  1. stirringThe mixture was then stirred for 5 hours between 60°-70°
  2. additionpoured onto ice (500 g.)
  3. extractionThe mixture was extracted with ether (3 × 150 ml.)
  4. extractionextracted with water (5 × 100 ml.)
  5. dry with materialAfter drying the ether solution over sodium sulfate
  6. customthe desiccant was removed by filtration
  7. customthe ether was evaporated
  8. customUpon recrystallization of the residue with ethyl acetate, 3.8 g
  9. customof product was obtained
  10. customtwo further recrystallizations from methanol

Sources & evidence

ORD record
ord-6899bb00b8f6482582555e36ad027f65
Source dataset
uspto-grants-1977_02
Patent number
US04009181

Reaction notes

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