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Triethylamine → 1-(2,4-Dichloro-3-chloromethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

HRID 1699178
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HRID 1699178 반응식
[Cl:1][C:2]1[C:7]([CH2:8]O)=[C:6]([Cl:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][NH:17][C:18](=[O:31])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:30])[NH:28][CH3:29])=[CH:23][CH:22]=1.C(N(CC)CC)C.CS([Cl:43])(=O)=O>CN(C)C=O>[Cl:1][C:2]1[C:7]([CH2:8][Cl:43])=[C:6]([Cl:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][NH:17][C:18](=[O:31])[CH:19]=[CH:20][C:21]1[CH:22]=[CH:23][C:24]([C:27](=[O:30])[NH:28][CH3:29])=[CH:25][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 539366561-(2,4-Dichloro-3-hydroxymethylphenyl)2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

생성물 1

HCID 536667761-(2,4-Dichloro-3-chloromethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a mixture of 1-(2,4-dichloro-3-hydroxymethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (148 mg), triethylamine (0.11 ml) and anhydrous dimethylformamide (1 ml) was added a 1M solution of methanesulfonyl chloride in dimethylformamide (0.77 ml) under ice-water cooling. The mixture was stirred at ambient temperature for 4 hours and partitioned between chloroform and saturated aqueous solution of sodium hydrogen carbonate. The organic layer was isolated, dried over magnesium sulfate and evaporated in vacuo to give a brown oil. The residue was purified by preparative thin layer chromatography (chloroform-methanol) to give 1-(2,4-dichloro-3-chloromethylphenyl)-2-[4-(methylcarbamoyl)cinnamoylaminomethyl]pyrrole (120 mg) as an amorphous powder.

후처리

  1. custompartitioned between chloroform and saturated aqueous solution of sodium hydrogen carbonate
  2. customThe organic layer was isolated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give a brown oil
  6. customThe residue was purified by preparative thin layer chromatography (chloroform-methanol)

출처 및 근거

ORD 기록
ord-2c83f4ef2ea54104a0ddf439b0b65867
출처 데이터셋
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06344462B1

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