Toluene → Methyl 3-[(cyclopropylamino)carbonyl]benzoate

HRID 502964Notes

Reaction equation

HRID 502964 reaction equation
[C:1]1([CH3:7])C=CC=C[CH:2]=1.[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([C:18]([OH:20])=O)[CH:15]=[CH:16][CH:17]=1)=[O:11].S(Cl)(Cl)=O.C[N:26](C=O)C>C(Cl)(Cl)Cl>[CH:1]1([NH:26][C:18]([C:14]2[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=2)[C:10]([O:9][CH3:8])=[O:11])=[O:20])[CH2:2][CH2:7]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 6018803-(Methoxycarbonyl)benzoic acid

Product 1

HCID 47231565Methyl 3-[(cyclopropylamino)carbonyl]benzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Toluene solution of 3-(Methoxycarbonyl)benzenecarboxylic acid, thionyl chloride and DMF (a catalytic amount) were heated under stirring. The reaction solution was dissolved in chloroform after evaporation under reduced pressure. After cyclopropylamine and triethylamine were added thereto and the whole was stirred at room temperature to obtain methyl 3-[(cyclopropylamino)carbonyl]benzoate.

Workup

  1. customafter evaporation under reduced pressure
  2. additionAfter cyclopropylamine and triethylamine were added
  3. stirringthe whole was stirred at room temperature

Sources & evidence

ORD record
ord-7970b8c847374f64b42bda5eaa1518c8
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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