1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2-Bromobenzyl)-2,2-diethoxyacetamide

HRID 40674

Reaction equation

HRID 40674 reaction equation
CN(C)CCCN=C=NCC.[Br:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH2:16].[CH2:21]([O:23][CH:24]([O:28][CH2:29][CH3:30])[C:25]([O-])=[O:26])[CH3:22].[Na+].O.ON1C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH:16][C:25](=[O:26])[CH:24]([O:28][CH2:29][CH3:30])[O:23][CH2:21][CH3:22]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 3340722-BromobenzylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 23663712Sodium diethoxyacetate

Product 1

HCID 59636401N-(2-Bromobenzyl)-2,2-diethoxyacetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide (1.15 g, 6.00 mmol) was added to a mixture of 2-bromobenzylamine (0.744 g, 4.00 mmol), sodium 2,2-diethoxyacetate (0.816 g, 4.80 mmol), 1-hydroxybenzotriazole hydrate (0.919 g, 6.00 mmol) and Hunig's base (1.53 mL, 8.80 mmol) in DMF (10 mL) with stirring. After 18 hours at room temperature, the mixture was partitioned between water and ethyl acetate. The organic layer was washed successively with 2 M HCl, saturated sodium bicarbonate solution and brine, then dried (Na2SO4) and concentrated to a viscous colourless oil (1.02 g, 81%). LC-MS (1) Rt==2.23 min; m/z (ESI+) 316 & 318 (M+H+).

Workup

  1. customthe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed successively with 2 M HCl, saturated sodium bicarbonate solution and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to a viscous colourless oil (1.02 g, 81%)
  5. customRt==2.23 min

Sources & evidence

ORD record
ord-68febdba4f2f472fbba15dc96a7fbf5f
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Linked notes

Loading…