Thionyl Chloride → HCID 21548370, compound

HRID 1605103Notes

Reaction equation

HRID 1605103 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.S(Cl)(Cl)=O>CN(C)C=O.C(Cl)CCl>[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([O:24][C:13]3[CH:14]=[CH:15][C:10]([NH:9][C:1](=[O:8])[CH3:2])=[CH:11][CH:12]=3)=[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

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 538804839-Benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid

Product 1

HCID 21548370HCID 21548370, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of 9.6 g. of 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid, 15 ml. of thionyl chloride and two drops of dry dimethylformamide in 100 ml. of ethylene dichloride was stirred at room temperature for 7 hours. The mixture was evaporated to dryness under reduced pressure, at room temperature, and to the resulting residue was added a solution of 6 g. of 4-acetamidophenol in 50 ml. of dry pyridine. The solution was stirred at room temperature for 30 minutes and diluted with water. The resulting solid was collected by filtration to give 6.74 g. of the title compound; m.p. 166°-168°C. (ethyl alcohol).

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure, at room temperature
  2. additionto the resulting residue was added a solution of 6 g
  3. additiondiluted with water
  4. filtrationThe resulting solid was collected by filtration
  5. customto give 6.74 g

Sources & evidence

ORD record
ord-06fbdb0bdce64f3bb5a376619e6b0770
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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