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

HRID 267535

반응식

HRID 267535 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 (E 1cm 1% 637), 257 mμ (shoulder); N.M.R. (pyridine- d6) δ 2.22 (CH3), 3.57(4H, NCH2CH2N unresolved multiplet). Analysis: Calculated for C23H21ClN2O4S: C 60.4; H 4.6; N 6.1; Cl 7.8; S 7.0; Found: C 60.2; H 4.9; N 6.1; Cl 7.7; S 7.7.

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-5bc188ccd2404aabafc568d5aa22a4bb
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03943147

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