Dimethylamine → HCID 20747587, compound

HRID 1873996Notes

Reaction equation

HRID 1873996 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:13][NH:14][CH3:15].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CC#N>[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:14]([CH3:15])[CH3:13])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 114704-Acetylbenzoic AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 20747587HCID 20747587, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-acetylbenzoic acid (40 g, 244 mmol), 40% aqueous dimethylamine (33.0 g, 292 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (56.1 g, 292 mmol), 1-hydroxybenzotriazole hydrate (44.8 g, 292 mmol) and N,N-diisopropylethylamine (85 mL, 487 mmol) in CH3CN (400 mL) was stirred at room temperature for 15 h then concentrated. The residue was dissolved in ethyl acetate (1000 mL), washed with H2O (2×200 mL), brine (200 mL), dried (MgSO4) and concentrated to provide 4-acetyl-N,N-dimethylbenzamide (24 g). The crude product was taken to the next step without purification.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (1000 mL)
  3. washwashed with H2O (2×200 mL), brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a41c624553a4bc284747653420509f9
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

Loading…