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2-Propanethiol → Methyl 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoate

HRID 2226857
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HRID 2226857 반응식
[CH3:1][CH:2]([SH:4])[CH3:3].Cl[C:6]1[C:7]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:8]=2[S:9][C:10]=1[C:11]([NH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)=[O:12].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C=O)C.C(OCC)(=O)C>[CH3:29][O:28][C:26]1[CH:25]=[CH:24][C:8]2[S:9][C:10]([C:11]([NH:13][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)=[O:12])=[C:6]([S:4][CH:2]([CH3:3])[CH3:1])[C:7]=2[CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 63642-PropanethiolHCID 19225607Methyl 4-[[[3-chloro-5-methoxybenzo[b]thien-2yl]carbonyl]amino]benzoateHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

생성물 1

HCID 18963770Methyl 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoate수율 72%

시약·촉매·용매 2

HCID 6228Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

2-Propanethiol (32 μL, 0.35 mmol) is added to a solution of methyl 4-[[[3-chloro-5-methoxybenzo[b]thien-2yl]carbonyl]amino]benzoate (100 mg, 0.27 mmol) in 1 mL of DMF. Diazabicycloundecene (DBU) (52 μL, 0.35 mmol) is added and the mixture is stirred at room temperature for 5 hours. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane gives methyl 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoate in 72% yield; mp=157.5°-158.5° C.

후처리

  1. washwashed with 1N HCl, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationFiltration
  4. concentrationfollowed by concentration in vacuo and recrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-70154838cbbe48dc97a89109d2f02ab7
출처 데이터셋
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05350748

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