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

HRID 267535

反応式

HRID 267535 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5bc188ccd2404aabafc568d5aa22a4bb
出典データセット
uspto-grants-1976_03
特許番号
US03943147

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