Oxalyl chloride → HCID 86745860, compound

HRID 1197122Notes

Reaction equation

HRID 1197122 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[CH:14]([CH3:17])[N:15]=[N:16][C:12]3=[CH:11][N:10]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:8]=2[CH:25]=1)([OH:3])=O.C(Cl)(=O)C([Cl:29])=O>ClCCl>[Cl:29][C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[CH:14]([CH3:17])[N:15]=[N:16][C:12]3=[CH:11][N:10]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:8]=2[CH:25]=1)=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 67899853HCID 67899853, compound

Product 1

HCID 86745860HCID 86745860, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.5 g (0.01 mol) of 8-carboxy-6-(2-chlorophenyl)-1-methyl[1,2,4]triazolo-[4,3-a][1,4]benzodiazepine are suspended in 40 ml of dichloromethane. While cooling in ice, 2.5 g (0.02 mol) of oxalyl chloride are added dropwise, and the mixture is stirred at room temperature for 2 hours. It is then concentrated and subsequently distilled twice with anhydrous chloroform. The crystalline residue is triturated with petroleum ether and filtered off with suction. 3.7 g (100%) of 8-chlorocarbonyl-6-(2-chlorophenyl)-1-methyl[1,2,4]- triazolo[4,3-a][1,4]benzodiazepine of melting point 295°-297° C. are obtained.

Workup

  1. temperatureWhile cooling in ice
  2. concentrationIt is then concentrated
  3. distillationsubsequently distilled twice with anhydrous chloroform
  4. customThe crystalline residue is triturated with petroleum ether
  5. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-e9cc866da5654f22a17be52f26d205b4
Source dataset
uspto-grants-1992_05
Patent number
US05116971

Reaction notes

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