3-Methylbenzaldehyde → 5-{1-[4-(3-Methyl-benzylamino)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester

HRID 30236

反応式

HRID 30236 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4].[C:22]1([CH3:30])[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=O)[CH:23]=1.C([BH3-])#N.[Na+].[Cl-].[NH4+]>O.C1COCC1.C(O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:21])[NH:11][CH:12]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][CH2:30][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=3)=[CH:18][CH:19]=2)[CH3:13])=[CH:8][CH:9]=1)=[O:4]

参加物

8

反応物 4

HCID 121053-MethylbenzaldehydeHCID 25517Ammonium ChlorideHCID 5003444Sodium cyanoborohydrideHCID 691350895-[1-(4-Amino-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester

生成物 1

HCID 691344495-{1-[4-(3-Methyl-benzylamino)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester収率 43%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 304.0 mg (1.0 mmol) 5-[1-(4-amino-phenyl)-ethylcarbamoyl]-thiophene-2-carboxylic acid methyl ester, 120.0 mg (1.0 mmol) m-tolualdehyde and 2 ml ethanol was heated under reflux for 1 h. The solvent was evaporated and 3 ml THF and 315 mg (5.0 mmol) sodium cyanoborohydride were added to the residue. After 18 h 5 ml aqueous ammonium chloride solution and 10 ml water were added. The aqueous phase was extracted with dichloromethane, the combined organic phases were dried over magnesium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (ethyl acetate/petrol ether 1:1) to yield 175 mg (0.43 mmol) 5-{1-[4-(3-Methyl-benzylamino)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. customThe solvent was evaporated
  4. extractionThe aqueous phase was extracted with dichloromethane
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-438e5106c59f43a0b80eee81d9de075a
出典データセット
uspto-grants-2008_09
特許番号
US07423060B2

関連ノート

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