Dimethylformamide → 3-Isopropylthio-4-methoxybenzoyl chloride

HRID 1584956Notes

Reaction equation

HRID 1584956 reaction equation
[CH:1]([S:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8](O)=[O:9])([CH3:3])[CH3:2].CN(C)C=O.S(Cl)([Cl:23])=O>C1(C)C=CC=CC=1>[CH:1]([S:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([Cl:23])=[O:9])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 21187827HCID 21187827, compound

Product 1

HCID 211879093-Isopropylthio-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-isopropylthio-4-methoxybenzoic acid (2.5 g; that is prepared as described in Reference Example 49) in toluene (25 mL), and dimethylformamide (0.2 mL) is treated with thionyl chloride (2.5 mL) and the solution is stirred at 60° C. for 3 hours. The solution is concentrated, treated with toluene (10 mL) and again evaporated to dryness, to give 3-isopropylthio-4-methoxybenzoyl chloride (2.7 g), in the form of a light brown oil.

Workup

  1. customthat is prepared
  2. concentrationThe solution is concentrated
  3. additiontreated with toluene (10 mL)
  4. customagain evaporated to dryness

Sources & evidence

ORD record
ord-b714d8aa4e6542b6a3e04c7e445e9ef0
Source dataset
uspto-grants-1999_08
Patent number
US05935978

Reaction notes

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