Triethylamine → 2-Chloro-5-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methylthio]benzoic acid

HRID 867974Notes

Reaction equation

HRID 867974 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5](=[O:9])[O:6][C:7]=1[CH3:8].[Cl:10][C:11]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C(N(CC)CC)C.C(Cl)(Cl)Cl.CO>ClCCl>[Cl:10][C:11]1[CH:19]=[CH:18][C:17]([S:20][CH2:2][C:3]2[O:4][C:5](=[O:9])[O:6][C:7]=2[CH3:8])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 98555184-(Chloromethyl)-5-methyl-1,3-dioxol-2-oneHCID 150863462-Chloro-5-sulfanylbenzoic acidHCID 21584188Chloroform methanol

Product 1

HCID 142755782-Chloro-5-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methylthio]benzoic acidYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 80 ml of dichloromethane was dissolved 4.0 g of 4-chloromethyl-5-methyl-1,3-dioxol-2-one, and 5.1 g of 2-chloro-5-mercaptobenzoic acid (synthesized in accordance with the method described in Swiss Pat. No. 426,865, C.A. 68.P68728c (1968)] was added. Then, 5.6 g of triethylamine was added, and the mixture was stirred at room temperature for 1 hour. After the reaction, the solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure silica gel column chromatography as in Example 1 [except that the column was prepared by using chloroform/methanol (10/1, v/v)]. Fractions of the main product obtained were concentrated to dryness under reduced pressure and the residue was dissolved in chroroform, and shaken with dilute hydrochloric acid. The chloroform layer was concentrated to dryness under reduced pressure, and then the residue was recrystallized from ethanol to give 4.8 g of the captioned compound as colorless crystals.

Workup

  1. customsynthesized in accordance with the method
  2. addition68.P68728c (1968)] was added
  3. customAfter the reaction
  4. customthe solvent was evaporated under reduced pressure
  5. customwas prepared
  6. customFractions of the main product obtained
  7. concentrationwere concentrated to dryness under reduced pressure
  8. dissolutionthe residue was dissolved in chroroform
  9. stirringshaken with dilute hydrochloric acid
  10. concentrationThe chloroform layer was concentrated to dryness under reduced pressure
  11. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3b1bdd5b593042a4bd63e8e210cf5bba
Source dataset
uspto-grants-1988_10
Patent number
US04777267

Reaction notes

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