Oxalyl chloride → 3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-N-(5-methyl-1,3,4-oxadiazol-2-yl)-4-(trifluoromethyl)benzamide

HRID 1753724Notes

Reaction equation

HRID 1753724 reaction equation
[C:1]([N:3]=[S:4]([C:7]1[C:8]([O:20][CH3:21])=[C:9]([CH:13]=[CH:14][C:15]=1[C:16]([F:19])([F:18])[F:17])[C:10]([OH:12])=O)([CH3:6])=[O:5])#[N:2].[NH2:22][C:23]1[O:24][C:25]([CH3:28])=[N:26][N:27]=1.C(Cl)(=O)C(Cl)=O>N1C=CC=CC=1>[C:1]([N:3]=[S:4]([C:7]1[C:8]([O:20][CH3:21])=[C:9]([CH:13]=[CH:14][C:15]=1[C:16]([F:19])([F:18])[F:17])[C:10]([NH:22][C:23]1[O:24][C:25]([CH3:28])=[N:26][N:27]=1)=[O:12])([CH3:6])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 65578Oxalyl chloride2×HCID 20602505-Methyl-1,3,4-oxadiazol-2-amineHCID 897668943-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluormethyl)benzoic acid

Product 1

HCID 897670943-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-N-(5-methyl-1,3,4-oxadiazol-2-yl)-4-(trifluoromethyl)benzamideYield 2.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

350 mg (80% by weight; 0.869 mmol) of 3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluoromethyl)benzoic acid and 151 mg (1.52 mmol) of 2-amino-5-methyl-1,3,4-oxadiazole were initially charged in 10 ml of dry pyridine and cooled in an ice bath. 207 mg (1.63 mmol) of oxalyl chloride were added, and after 30 minutes the mixture was thawed to RT. The contents were stirred at RT for 2 h, and another 51.8 mg (0.408 mmol) of oxalyl chloride were then added. The mixture was then stirred at RT for 16 h. For work-up, the contents were freed from the solvent on a rotary evaporator and the residue was taken up in water and dichloromethane. After phase separation, the organic phase was freed from the solvent on a rotary evaporator and the residue was purified chromatographically under neutral conditions, which gave 9.80 mg of product.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe mixture was then stirred at RT for 16 h
  3. customFor work-up, the contents were freed from the solvent on a rotary evaporator
  4. customAfter phase separation
  5. customthe organic phase was freed from the solvent on a rotary evaporator
  6. customthe residue was purified chromatographically under neutral conditions, which

Sources & evidence

ORD record
ord-64f468ff0eed4e26945f2186dce8033e
Source dataset
uspto-grants-2015_10
Patent number
US09167819B2

Reaction notes

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