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Dibutyltin dichloride → 2-(4-Trifluoromethoxy-phenyl)-benzothiazole-6-carboxylic acid (2-aminophenyl)-amide

HRID 416241
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인쇄 미리보기

반응식

HRID 416241 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:20]2[N:21]=[C:22](N)[S:23][C:19]=2[CH:18]=1)=[O:16])(C)(C)C.[F:28][C:29]([F:40])([F:39])[O:30][C:31]1[CH:38]=[CH:37][C:34](C=O)=[CH:33][CH:32]=1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[CH:26]=[CH:25][C:20]2[N:21]=[C:22]([C:34]3[CH:33]=[CH:32][C:31]([O:30][C:29]([F:28])([F:39])[F:40])=[CH:38][CH:37]=3)[S:23][C:19]=2[CH:18]=1)=[O:16]
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참가 물질

6

반응물 4

HCID 12688Dibutyltin dichlorideHCID 12752Phenylsilane2회HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 58930649{2-[(2-Amino-benzothiazole-6-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

생성물 1

HCID 666221852-(4-Trifluoromethoxy-phenyl)-benzothiazole-6-carboxylic acid (2-aminophenyl)-amide수율 93.7%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 115 (300 mg, 0.78 mmol), 4-(trifluoromethoxy)benzaldehyde (123 μl, 0.86 mmol), and dibutyltin dichloride (24 mg, 0.08 mmol) in THF was added phenylsilane (106 μl, 0.86 mmol). The mixture was stirred overnight at room temperature under nitrogen, additional aldehyde and phenylsilane were added and the stirring continued until no more starting material was present. The THF was evaporated off the mixture and the residue was purified by flash column chromatography (EtOAc/hexane 30/70, then 50/50), to give the title compound 116 (314 mg, 72%). 1H-NMR (DMSO) δ: 9.77 (s, 1H), 8.89 (t, J=5.7 Hz, 1H); 8.69 (s, 1H); 8.29 (d, J=1.8 Hz, 1H); 7.84 (dd, J=8.4, 1.8 Hz, 1H); 7.50 (m, 5H); 7.37 (d, J=7.8 Hz, 2H); 7.17 (m, 2H); 4.69 (d, J=5.7 Hz, 2H); 1.47 (s, 9H).

후처리

  1. customThe THF was evaporated off the mixture
  2. customthe residue was purified by flash column chromatography (EtOAc/hexane 30/70

출처 및 근거

ORD 기록
ord-59ca4d0e133e41ba887e1831d0fefbac
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088805B2

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