Hydrochloric Acid → 2-[2-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid

HRID 1294281노트

반응식

HRID 1294281 반응식
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[OH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([O:33]C)=[O:32].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:14][C:13]1[S:12][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:10][C:9]=1[CH2:8][O:7][C:6]1[CH:21]=[CH:22][C:3]([CH2:2][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][C:31]([OH:33])=[O:32])=[CH:4][CH:5]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 178613534-(4-Chloromethylphenoxymethyl)-5-methyl-2-phenylthiazole

생성물 1

HCID 688842202-[2-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid수율 44.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenylthiazole (2.13 g), methyl 2-(2-hydroxyphenyl)acetate (1.00 g), anhydrous potassium carbonate (1.65 g) and N,N-dimethylformamide (15 mL) was stirred overnight at room temperature. The reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. To a mixture of the obtained residue, tetrahydrofuran (10 mL) and methanol (10 mL) was added a 1N aqueous sodium hydroxide solution (10 mL) and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated, and dilute hydrochloric acid was added to the residue. The precipitated solid was collected by filtration and dried with air to give crystals (1.19 g, 44%) of 2-[2-[4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]phenyl]acetic acid. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 122-123° C.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionTo a mixture of the obtained residue, tetrahydrofuran (10 mL) and methanol (10 mL)
  6. additionwas added a 1N aqueous sodium hydroxide solution (10 mL)
  7. stirringthe mixture was stirred at room temperature for 2 hrs
  8. concentrationThe reaction mixture was concentrated
  9. additiondilute hydrochloric acid was added to the residue
  10. filtrationThe precipitated solid was collected by filtration
  11. customdried with air

출처 및 근거

ORD 기록
ord-efaeae9f0ab84006979d1167e80a5a8b
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238716B2

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