Dimethylformamide → 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoyl chloride

HRID 2297540Notes

Reaction equation

HRID 2297540 reaction equation
S(Cl)([Cl:3])=O.CN(C=O)C.[CH3:10][C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=2)[N:12]=1>C1(C)C=CC=CC=1>[CH3:10][C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([Cl:3])=[O:21])=[CH:18][CH:17]=2)[N:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 71278084-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid

Product 1

HCID 71645884-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

46 ml of thionyl chloride and 1 ml of DMF are added to a solution of 10.0 g of 4-(5-methyl-1,2,4-oxadiazol-3-yl)benzoic acid in 150 ml of toluene. The solution is heated under reflux for 5 hours. The solvent is removed, giving 4-(5-methyl-1,2,4-oxadiazol-3-yl)-benzoyl chloride, EI 222. Subsequent reaction with 9.3 g of 1-tert-butoxycarbonylpiperazine in 150 ml of dichloromethane and 48 ml of triethylamine gives, after customary work-up, tert-butyl 4-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoyl]piperazine-1-carboxylate, FAB 373.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 5 hours
  3. customThe solvent is removed

Sources & evidence

ORD record
ord-59c6cfc95950462abf0e9f2aeeb426a4
Source dataset
uspto-grants-2002_12
Patent number
US06492368B1

Reaction notes

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