2,4,6-Trichlorobenzenesulfonyl chloride → 2,4,6-trichloro-N-[4-methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-yl]benzenesulfonamide

HRID 1245632

反応式

HRID 1245632 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([NH2:12])[S:5][C:6]=1[CH2:7][C:8]([Cl:11])([Cl:10])[Cl:9].[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[C:15]=1[S:22](Cl)(=[O:24])=[O:23]>>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[C:15]=1[S:22]([NH:12][C:4]1[S:5][C:6]([CH2:7][C:8]([Cl:11])([Cl:9])[Cl:10])=[C:2]([CH3:1])[N:3]=1)(=[O:24])=[O:23]

参加物

3

反応物 2

HCID 5213352,4,6-Trichlorobenzenesulfonyl chlorideHCID 156488254-Methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-ylamine

生成物 1

HCID 114092072,4,6-trichloro-N-[4-methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-yl]benzenesulfonamide収率 46%

実験手順

The title compound was prepared according to METHOD A from 4-methyl-5-(2,2,2-trichloroethyl)-1,3-thiazol-2-ylamine (123 mg, 0.5 mmol, prepared according to Dodinov, A. A et al (1993) Chem. Heterocycl. Comp (Eng. Transl.) 29(8): 955-958) and 2,4,6-trichlorobenzenesulfonyl chloride (140 mg, 0.5 mmol). The solution was allowed to stand at room temperature overnight. The solution was directly loaded on a silica gel column for flash column chromatography, eluted with a mixed solvent of ethyl acetate and hexane (up to 40% v/v) to give a solid product. Crystallization of the product from ethyl acetate and hexane gave the title compound as a white solid (112 mg, 46% yield): mp 228-229° C.; MS m/e 487, 489, 491, 493; Anal. Calcd. (found) for C12H8Cl6N2O2S2: C 29.5 (29.7) % H 1.7 (2.1) % N 5.7 (5.8) %.

後処理

  1. customThe title compound was prepared
  2. customprepared
  3. washeluted with a mixed solvent of ethyl acetate and hexane (up to 40% v/v)
  4. customto give a solid product
  5. customCrystallization of the product from ethyl acetate and hexane

出典と根拠

ORDレコード
ord-31c77c55b0174d7482390a1008b0753a
出典データセット
uspto-grants-2006_10
特許番号
US07125900B2

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