Thionyl Chloride → HCID 22596745, compound

HRID 1760734Notes

Reaction equation

HRID 1760734 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)(O)[C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[CH:17]=3)[N:12]([CH3:34])[C:11](=[O:35])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:38])=O>>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([Cl:38])([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[CH:17]=3)[N:12]([CH3:34])[C:11](=[O:35])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 22596744HCID 22596744, compound

Product 1

HCID 22596745HCID 22596745, compound

Conditions

Temperature
22 °C

Procedure

A 1 liter reaction vessel was charged with 105.4 g of 4-(3-chlorophenyl)-6-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone hydrochloric acid salt (compound (III) and 400 ml of N,N-dimethylimidazolidinone added at 22° C. The mixture was stirred vigorously for 15 minutes at 22° C. and became homogeneous. 32.1 ml of thionyl chloride was added over 10 minutes to the reaction mixture, the reaction temperature rising from 22° C. to 40° C. After addition of the thionyl chloride, the reaction mixture was cooled from 40° C. to 22° C. and stirred for three hours at the latter temperature to provide a solution of 4-(3-chlorophenyl)-6-[chloro-(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone (compound (IV).

Workup

  1. customA 1 liter reaction vessel
  2. additionadded at 22° C
  3. customrising from 22° C. to 40° C
  4. temperaturethe reaction mixture was cooled from 40° C. to 22° C.
  5. stirringstirred for three hours at the latter temperature

Sources & evidence

ORD record
ord-59530ac4fa734d6c98faff099e1a2829
Source dataset
uspto-grants-2005_01
Patent number
US06844439B2

Reaction notes

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