Thionyl Chloride → HCID 53973898, compound

HRID 1606158Notes

Reaction equation

HRID 1606158 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([N:12]([CH2:8][CH3:6])[CH2:11][CH3:10])=[O:17])=[CH:10][CH:9]=2)=[O:7])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10016371HCID 10016371, compound

Product 1

HCID 53973898HCID 53973898, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 6.1 g. (0.02 mole) of 5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetic acid in 100 ml. chloroform is added 3.8 ml. (0.03 mole) thionyl chloride. The mixture is stirred and refluxed overnight. The solvent is then evaporated and the residue is added quickly to a solution of 22 ml. diethylamine in 50 ml. water while cooling externally with an ice-bath. A solid precipitates, 5-(p-chlorobenzoyl)-N,N-diethyl-1-methylpyrrole-2-acetamide, which is collected and purified by recrystallization from methylcyclohexane (with charcoal while in solution), m.p. 82°-85°C.

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent is then evaporated
  3. additionthe residue is added quickly to a solution of 22 ml
  4. temperaturewater while cooling externally with an ice-bath
  5. customA solid precipitates
  6. custom5-(p-chlorobenzoyl)-N,N-diethyl-1-methylpyrrole-2-acetamide, which is collected
  7. custompurified by recrystallization from methylcyclohexane (with charcoal while in solution), m.p. 82°-85°C.

Sources & evidence

ORD record
ord-69de866dc2394396930dbfee45f30fcf
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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