Dimethylformamide → 3-Isopropylthio-4-methoxybenzoyl chloride

HRID 356944Notes

Reaction equation

HRID 356944 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-479cb8202c3a43b2a9ac5fa5b2f168bd
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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