2-(4'-Chlorobenzoyl)benzoic acid → 3-(p-Chlorophenyl)-3-[2-(4-methylphenylsulfonylamino)ethylamino]phthalide

HRID 259160

반응식

HRID 259160 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24].[K+].[Br-]>C(O)C.O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2([NH:19][CH2:20][CH2:21][NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=[O:12])[O:7]2)=[CH:17][CH:18]=1

참가 물질

7

반응물 3

HCID 665642-(4'-Chlorobenzoyl)benzoic acidHCID 253877Potassium BromideHCID 301318N-(2-Aminoethyl)-4-methylbenzenesulfonamide

생성물 1

HCID 214233433-(p-Chlorophenyl)-3-[2-(4-methylphenylsulfonylamino)ethylamino]phthalide

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 1140Toluene용매

실험 절차

To a flask equipped with a Dean-Stark water separator is charged 500 ml. of toluene, 24.0 g. (0.10 mole) of 2-(p-chlorobenzoyl) benzoic acid and 21.4 g. (0.10 mole) of N-(2-aminoethyl)-4-methylbenzene sulfonamide. The mixture is stirred and refluxed until the water level in the separator is constant. The reaction is then allowed to cool to room temperature and the resultant solid is filtered off, washed with 100 ml. of toluene and dried to give the above named phalide; m.p. 177°-179° C.: infrared (KBr), peaks at 3.00, 3.09, 3.37, 3.42, 3.48, 5.76, 6.25, 6.71, 7.42, 7.72, 8.58, 9.12, 9.90, 11.45, 12.80, 13.70, 17.30 and 18.20μ; ultraviolet (95% ethanol) maximum at 226 mμ (E1cm1% 637), 257 mμ (shoulder); N.M.R. (pyridine- d6) δ 2.22 (CH3), 3.57(4H, NCH2CH2N unresolved multiplet).

후처리

  1. additionis charged 500 ml
  2. filtrationthe resultant solid is filtered off
  3. washwashed with 100 ml
  4. dry with materialof toluene and dried
  5. customto give the above named phalide

출처 및 근거

ORD 기록
ord-e7f59f3a4b1a4d2eb75e4e9b5a9bfd22
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04036855

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