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4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-{4-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenoxysulfonyl}-2-hydroxy-benzoic Acid

HRID 1871324
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HRID 1871324 반응식
[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].Cl[S:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([OH:36])[CH:28]=1)(=[O:26])=[O:25]>>[CH2:1]([C:5]1[O:6][C:7]2[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=2[C:9]=1[CH2:10][NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][S:24]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([OH:36])[CH:28]=2)(=[O:26])=[O:25])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]
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참가 물질

3

반응물 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 234456414-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenol

생성물 1

HCID 101414894-{4-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenoxysulfonyl}-2-hydroxy-benzoic Acid수율 85%

실험 절차

The title compound was prepared according to the procedure in Example 4 using 4-[(2-butyl-benzofuran-3-ylmethyl)-amino]-phenol (0.500 g, 1.69 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.401 g, 1.69 mmol). Purification on 2% H3PO4 /MeOH treated silica gel, eluting with 25% EtOAc/hexane gave 0.571 g (85%) of the title compound as a dark yellow solid, mp 75-77° C. 1H NMR (DMSO-d6) δ 0.86 (t, 3 H), 1.31 (sextet, 2 H), 1.60 (quintet, 2 H), 2.80 (t, 2 H), 4.23 (s, 2 H), 6.54 (d, 2 H), 6.72 (d, 2 H), 7.14-7.22 (m, 2 H), 7.26-7.30 (m, 2 H), 7.45 (dd, 1 H), 7.58 (dd, 1 H), 7.95 (d, 1 H). IR (KBr) 3400, 2950, 1600, 1510 and 1380 cm-1. mass spectrum (-ESI) m/z 494 (M-H).

후처리

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4 /MeOH
  3. additiontreated silica gel
  4. washeluting with 25% EtOAc/hexane

출처 및 근거

ORD 기록
ord-0775c6972ea74fc5b858577944c2211e
출처 데이터셋
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06103708

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