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4-Nitrophenol → HCID 178512722、化合物

HRID 615913
ノート
印刷プレビュー

反応式

HRID 615913 の反応式
Cl.Cl.[NH:3]([C:7]1[S:8][CH:9]=[C:10]([CH2:12][S:13][CH2:14][CH2:15][NH2:16])[N:11]=1)[C:4]([NH2:6])=[NH:5].[C:17]1([S:23]([NH:26][C:27]2[CH:28]=[C:29]([CH:42]=[CH:43][CH:44]=2)[C:30](OC2C=CC([N+]([O-])=O)=CC=2)=[O:31])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(S(NC2C=C(C=CC=2)C(O)=O)(=O)=O)C=CC=CC=1.[N+](C1C=CC(O)=CC=1)([O-])=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(N(CC)CC)C>[C:17]1([S:23]([NH:26][C:27]2[CH:28]=[C:29]([CH:42]=[CH:43][CH:44]=2)[C:30]([NH:16][CH2:15][CH2:14][S:13][CH2:12][C:10]2[N:11]=[C:7]([NH:3][C:4]([NH2:6])=[NH:5])[S:8][CH:9]=2)=[O:31])(=[O:24])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 7922013-Benzenesulfonamidobenzoic acidHCID 541944984-Nitrophenyl 3-[(benzenesulfonyl)amino]benzoateHCID 178478806HCID 178478806、化合物

生成物 1

HCID 178512722HCID 178512722、化合物収率 83.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
40 °C

実験手順

A mixture of 5.5 g of 2-(2-guanidinothiazol-4-ylmethylthio)ethylamine dihydrochloride, 3.65 g of triethylamine and 3.7 g of 4-nitrophenyl 3-benzenesulfonamidobenzoate (m.p. 175°-178° C., prepared from 3-benzenesulfonamidobenzoic acid and 4-nitrophenol in methylene chloride in the presence of dicyclohexylcarbodiimide) is stirred at the temperature of 40° C. for 90 minutes, then it is evaporated under reduced pressure to dryness. The residue is taken up with 150 ml of ethyl acetate and washed twice with 10 ml of water. The solution is dried on anhydrous sodium sulfate, evaporated and the residue is chromatographied on silica with a chloroform:ethanol 4:1 mixture. Thus, 3.8 g of 3-benzenesulfonamido-N-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]benzamide are obtained as an oil which is dissolved in absolute ethanol and treated with fumaric acid in absolute ethanol. Thus, 3.6 g of crude product are obtained, which, after crystallization from 40 ml of 95% ethanol, gives 2.4 g of neutral fumarate of 3-benzenesulfonamido-N-[2-(2-guanidinothiazol-4-ylmethylthio)ethyl]benzamide, SR 57963 A, C20H22N6O3S4.1/2C4H4O4 ; m.p. 139°-141° C.

後処理

  1. customit is evaporated under reduced pressure to dryness
  2. washwashed twice with 10 ml of water
  3. dry with materialThe solution is dried on anhydrous sodium sulfate
  4. customevaporated

出典と根拠

ORDレコード
ord-73c76ef609a842048fecc2a250e80b2c
出典データセット
uspto-grants-1985_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04501747

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート