Water → 4-(3-Benzyloxy-propyl)-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

HRID 2263440노트

반응식

HRID 2263440 반응식
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[S:15][C:16]=1[CH2:17]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS([Cl:33])(=O)=O.C(N(CC)CC)C.O>ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[S:15][C:16]=1[CH2:17][Cl:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59296181[4-(3-Benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol

생성물 1

HCID 595946804-(3-Benzyloxy-propyl)-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole수율 53.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 1.5 g of {4-[3-(benzyloxy)propyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol in 15 mL of dichloromethane were added 0.484 g of methanesulfonylchloride and 1.03 mL of triethylamine. The solution was stirred for 2 h at room temperature. The mixture was diluted with dichloromethane and poured into water. The aqueous layer was separated and extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 1.65 g of crude product as a yellow oil. Purification by column chromatography on silica gel (heptane 90/ethyl acetate 10) gave 0.840 g of 4-(3-benzyloxy-propyl)-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole.

후처리

  1. customThe aqueous layer was separated
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give 1.65 g of crude product as a yellow oil
  7. customPurification by column chromatography on silica gel (heptane 90/ethyl acetate 10)

출처 및 근거

ORD 기록
ord-1acc31fc7f6241d1a75a89672d68cc3e
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851493B2

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