Thionyl Chloride → HCID 87998386, compound

HRID 23878Notes

Reaction equation

HRID 23878 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:20][CH:19]3[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)[CH:13]2[C:21](O)=[O:22])(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.O=S(Cl)[Cl:26]>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH2:20][CH:19]3[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)[CH:13]2[C:21]([Cl:26])=[O:22])(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 22569209N-(3,5-Dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acid

Product 1

HCID 87998386HCID 87998386, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

N-(3,5-Dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acid (1 gm, 2.64 mmol) was dissolved in CH2Cl2 (5 mL) containing DMF (1 drop) and SOCl2 (770 μL, 10.56 mmol). The reaction mixture was refluxed under nitrogen for ˜1 hr. The reaction mixture was monitored by TLC for the formation of the acid chloride. The reaction mixture was then concentrated in vacuo and azeotroped with toluene (1×5 mL) to afford N-(3,5-dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acid chloride which was used without further purification in the subsequent step.

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for ˜1 hr
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customazeotroped with toluene (1×5 mL)

Sources & evidence

ORD record
ord-f365d521b5b54e1493008a822705eacd
Source dataset
uspto-grants-2005_02
Patent number
US06855708B2

Reaction notes

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