Dimethylamine → Methyl 4-(dimethylcarbamoyl)benzoate

HRID 970393Notes

Reaction equation

HRID 970393 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=[O:6]>C1COCC1>[CH3:1][N:2]([CH3:3])[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoate

Product 1

HCID 11106558Methyl 4-(dimethylcarbamoyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.2 30 ml of a 40% dimethylamine solution in 200 ml of THF are initially introduced. 20 g of methyl 4-chlorocarbonylbenzoate are dissolved in 300 ml of THF and added dropwise, and the mixture is stirred at room temperature for a further 2 hours. The solvent is removed, and the mixture is subjected to conventional work-up, giving 19.2 g of methyl 4-(N,N-dimethylaminocarbonyl)benzoate (“BB”), m.p. 107°.

Workup

  1. additionadded dropwise
  2. customThe solvent is removed

Sources & evidence

ORD record
ord-cb71bfcfeaa64fdeae6a086d0820cd34
Source dataset
uspto-grants-2007_12
Patent number
US07312224B2

Reaction notes

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