Benzyl Chloride → HCID 21548342, compound

HRID 1605088Notes

Reaction equation

HRID 1605088 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]([C:14]([OH:16])=[O:15])[CH2:3][CH2:2]1.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 21514240HCID 21514240, compound

Product 1

HCID 21548342HCID 21548342, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 13 g. 1,2,3,4-tetrahydrocarbazole-4-carboxylic acid, 7.8 g. benzyl chloride and 6.5 g. sodium carbonate in dry dimethylformamide was heated on a steam bath for one hour and filtered. The dimethylformamide was evaporated under reduced pressure and the resulting oil was taken up in ether. The ether solution was washed with water, dried and evaporated to give, after recrystallization, 15.5 g. of the title compound, m.p. 108°-112°C. (heptane).

Workup

  1. additionA stirred mixture of 13 g
  2. filtrationfiltered
  3. customThe dimethylformamide was evaporated under reduced pressure
  4. washThe ether solution was washed with water
  5. customdried
  6. customevaporated
  7. customto give
  8. customafter recrystallization, 15.5 g

Sources & evidence

ORD record
ord-92fc7bc2d84345848acade988e84e16b
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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