2-chloro-N-methylacetamide → HCID 66591486, compound

HRID 2264658Notes

Reaction equation

HRID 2264658 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][NH:17][CH2:18][C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24][CH2:25][C:26]([NH:28][CH3:29])=[O:27].C(N(C(C)C)CC)(C)C>C(#N)C.Cl.C(OCC)(=O)C>[ClH:24].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][N:17]([CH2:18][C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[CH2:25][C:26]([NH:28][CH3:29])=[O:27])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 667732-chloro-N-methylacetamideHCID 81531DiisopropylethylamineHCID 59596827HCID 59596827, compound

Product 1

HCID 66591486HCID 66591486, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.0 g (9.8 mmol) of [2-(3-benzyloxy-phenyl)-ethyl]-(furan-2-ylmethyl)amine, 15.0 g (10.7 mmol) of 2-chloro-N-methyl-acetamide and 1.87 ml (10.7 mmol) of diisopropylethylamine in 50 ml of acetonitrile was stirred under reflux for 24 hours. The solvent was removed under reduced pressure and the crude reaction mixture was purified by flash chromatography (ethyl acetate/hexane 1:1 v:v). The product isolated was dissolved in anhydrous hydrochloric acid in ethyl acetate. The solvent was removed under vacuum and the residue was triturated with diethyl ether. 2.66 g (65% yield) of the title compound were isolated as a hygroscopic solid.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe crude reaction mixture
  4. customwas purified by flash chromatography (ethyl acetate/hexane 1:1 v:v)
  5. customThe product isolated
  6. customThe solvent was removed under vacuum
  7. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8a5ebfa5d96943b58119858d1d504a29
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

Loading…