Thionyl Chloride → 5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoyl chloride

HRID 2075952Notes

Reaction equation

HRID 2075952 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:17]=1)[C:14](O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:28])=O>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:17]=1)[C:14]([Cl:28])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 670964845-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoic acid

Product 1

HCID 866472275-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoic acid (reference example 5-1) (817 mg), thionyl chloride (0.53 mL), N,N-dimethylformamide (1 drop) and toluene (10 mL) was stirred at 80° C. for 30 minutes. The mixture was concentrated under reduced pressure. Toluene was added to the residue, and the mixture was concentrated under reduced pressure to give 5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)benzoyl chloride.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionToluene was added to the residue
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9b398c98b86d4b3fbd809b50db554ac8
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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