Diethylamine → N,N-diethyl-4-formylbenzamide

HRID 1837543Notes

Reaction equation

HRID 1837543 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)=[O:2].[CH2:12]([N:14](CC)[CH2:15][CH3:16])[CH3:13].C(OC(Cl)=O)C(C)C.C(NCC)C>C1COCC1>[CH2:12]([N:14]([CH2:15][CH3:16])[C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][CH:10]=1)[CH3:13]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 120884-Formylbenzoic acidHCID 62365Isobutyl chloroformate

Product 1

HCID 10954698N,N-diethyl-4-formylbenzamideYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Formylbenzoic acid (11.2 g, 74.6 mmol) and triethylamine (10.4 mL, 75 mmol) was dissolved in THF (100 mL) and cooled to −10° C. i-Butylchloroformate (10.3 mL, 78 mmol) was added and stirring was continued for 10 minutes at −10° C. before diethylamine (9.7 mL, 94 mmol) was added and solution was allowed to reach 25° C. After concentration, aqueous workup and chromatography on silica (0-100% EtOAc in heptane), a total of 7.4 g (50%) compound I was obtained.

Workup

  1. additionwas added
  2. additionwas added
  3. customto reach 25° C
  4. concentrationAfter concentration, aqueous workup and chromatography on silica (0-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-6b7675beecea4ba4978d7467afe8c74b
Source dataset
uspto-grants-2004_08
Patent number
US06784181B2

Reaction notes

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