Diethylamine → N,N-Diethyl-2,3-dimethylbenzamide

HRID 717065Notes

Reaction equation

HRID 717065 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:12]([N:15](CC)[CH:16](C)[CH3:17])(C)[CH3:13].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(NCC)C>C(Cl)Cl.CN(C=O)C>[CH2:12]([N:15]([CH2:16][CH3:17])[C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[CH3:1])[CH3:13]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 117822,3-Dimethylbenzoic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 15621069N,N-Diethyl-2,3-dimethylbenzamideYield 72%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a stirred solution of 2,3-dimethyl-benzoic acid (1.52 g, 10.1 mmol) in CH2Cl2/DMF (118 mL/12 mL) was added N,N-diisopropylethylamine (1.76 mL, 10.1 mmol) and TBTU (3.25 g, 10.1 mmol) and the reaction mixture stirred at RT for 50 min. N,N-diethylamine (1.58 mL, 15.2 mmol) was added and the reaction mixture stirred for 18 h. The reaction mixture was washed with 10% Na2CO3 solution (2×100 mL) and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with isohexane and increasing the polarity to 30% EtOAc/isohexane to obtain N,N-diethyl-2,3-dimethyl-benzamide as a colourless liquid (1.48 g, 72%).

Workup

  1. stirringthe reaction mixture stirred for 18 h
  2. washThe reaction mixture was washed with 10% Na2CO3 solution (2×100 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with isohexane
  6. temperatureincreasing the polarity to 30% EtOAc/isohexane

Sources & evidence

ORD record
ord-d0c4a286863a4091bd5a4a96c43c8ff0
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

Loading…