Thionyl Chloride → HCID 10782340, compound

HRID 355927Notes

Reaction equation

HRID 355927 reaction equation
[CH3:1][C:2]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[C:9]([Cl:16])[CH:8]=1)=[O:5].S(Cl)([Cl:24])=O>>[CH3:1][C:2]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([Cl:24])=[O:12])=[C:9]([Cl:16])[CH:8]=1)=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 54102672HCID 54102672, compound

Product 1

HCID 10782340HCID 10782340, compound

Procedure

A mixture of 1.85 g of 4-[(2-methyl-3-fluorobenzoyl)amino]-2-chlorobenzoic acid in 30 ml of thionyl chloride under argon is heated at reflux for 1 hour. The thionyl chloride is evaporated in vacuo to a residue which is stirred with hexane and collected to give 1.94 g of 4-[(2-methyl-3-fluorobenzoyl)amino]-2-chlorobenzoyl chloride which is dissolved in 25 ml of methylene chloride and 0.49 g of N,N-diisopropylethylamine added, followed by 0.65 g of 6,11-dihydro-5H-dibenz[b,e]azepine. The reactants are stirred at room temperature for 18 hours and washed with water, saturated NaHCO3, dried (Na2SO4) and passed through a short pad of hydrous magnesium silicate to give 1.19 g of the desired product as a glass.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. customThe thionyl chloride is evaporated in vacuo to a residue which
  4. customcollected

Sources & evidence

ORD record
ord-25fa166ff4a44531adff7e1fd4c069be
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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