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

HRID 867974
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HRID 867974 반응식
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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3b1bdd5b593042a4bd63e8e210cf5bba
출처 데이터셋
uspto-grants-1988_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04777267

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