Thionyl Chloride → HCID 20400791, compound

HRID 1980856Notes

Reaction equation

HRID 1980856 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[N:11]([CH3:19])[C:10]=1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)(O)=[O:2].S(Cl)([Cl:28])=O>C1(C)C=CC=CC=1>[Cl:28][C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[N:11]([CH3:19])[C:10]=1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 129519HCID 129519, compound

Product 1

HCID 20400791HCID 20400791, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 1.52 g of 3-(5-carboxypentyl)-5-chloro-1-methyl-2-(3-pyridyl)indole in 50 ml of toluene under nitrogen is added dropwise at room temperature 0.31 ml of thionyl chloride. The resulting mixture is heated under reflux for 1 hour. An additional 0.10 ml portion of thionyl chloride is added and the solution is stirred at room temperature overnight. The resulting suspension is evaporated to dryness to give 3-(5-chlorocarbonylpentyl)-5-chloro-1-methyl-2-(3-pyridyl)indole. A suspension of the acid chloride in 20 ml of concentrated ammonium hydroxide is stirred at room temperature overnight. The resulting solid is filtered off to yield 3-(5-carbamoylpentyl)-5-chloro-1-methyl-2-(3-pyridyl)indole.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureunder reflux for 1 hour
  3. customThe resulting suspension is evaporated to dryness

Sources & evidence

ORD record
ord-c9af8b149b7940378113a6a7085ae0cc
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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