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

HRID 30236
Notes
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Reaction equation

HRID 30236 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-438e5106c59f43a0b80eee81d9de075a
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07423060B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes