Oxalyl chloride → HCID 23502546, compound

HRID 1835055Notes

Reaction equation

HRID 1835055 reaction equation
[Cl:1][C:2]1[C:17]([CH2:18][S:19][C:20]2[N:24]([CH3:25])[N:23]=[N:22][N:21]=2)=[C:16]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:15]=[CH:14][C:3]=1[C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:7]1=O)=[O:5].C(Cl)(=O)C([Cl:33])=O>ClCCl.CN(C)C=O>[Cl:33][C:7]1[CH2:8][CH2:9][CH2:10][C:11](=[O:12])[C:6]=1[C:4](=[O:5])[C:3]1[CH:14]=[CH:15][C:16]([S:26]([CH3:29])(=[O:28])=[O:27])=[C:17]([CH2:18][S:19][C:20]2[N:24]([CH3:25])[N:23]=[N:22][N:21]=2)[C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 23502623HCID 23502623, compound

Product 1

HCID 23502546HCID 23502546, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{2-chloro-4-methylsulfonyl-3-{[(1-methyl-1Htetrazol-5-yl)thio]-methyl}benzoyl}cyclohexane-1,3-dione (1.0 g) in dichloromethane (100 ml), oxalyl chloride (0.91 g) and 2 drops of N,N-dimethylformamide were added dropwise and the mixture was refluxed for 3 hours. The residue obtained by distilling off the solvent after the reaction was purified by silica gel column chromatography (eluant:ethyl acetate:hexane=7:3) to obtain the objective 3-chloro2-{2-chloro-4-methylsulfonyl-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}benzoyl}-2-cyclohexen-1-one (0.71 g). IR (NaCl):=1662,1310,1279, 1150 cm−1.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe residue obtained
  3. distillationby distilling off the solvent after the reaction
  4. customwas purified by silica gel column chromatography (eluant:ethyl acetate:hexane=7:3)

Sources & evidence

ORD record
ord-7335788ef4bc4f20a483c7a4ff785875
Source dataset
uspto-grants-2004_08
Patent number
US06770599B2

Reaction notes

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