1,2-Dichloroethane → HCID 22326844, compound

HRID 491619Notes

Reaction equation

HRID 491619 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][C:13]([OH:15])=O.C(Cl)CCl.C[CH2:21][N:22](CC)[CH2:23]C.Cl.CNC>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][C:13]([N:22]([CH3:23])[CH3:21])=[O:15]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 35192982-(2-methoxy-5-nitrophenyl)acetic acid

Product 1

HCID 22326844HCID 22326844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(2-Methoxy-5-nitrophenyl)acetic acid (17.1 g, 1 eq, Step B), EDC (18.6 g, 1.2 eq.), Et3N (9.8 g, 13.6 mL, 1.2 eq) and dimethylamine hydrochloride (7.9 g, 1.2 eq.) in 150 mL of CH2Cl2 were stirred together with exclusion of air overnight. CH2Cl2 (150 mL) was added and the mixture was washed twice with 1M HCl, twice with 1M NaOH, H2O and brine. Removal of the solvent under reduced pressure followed by silica gel chromatography (90:10 CH2Cl2:EtOAc) afforded pure 2-(2-methoxy-5-nitrophenyl)-N,N-dimethyl-acetamide as a white solid.

Workup

  1. washthe mixture was washed twice with 1M HCl, twice with 1M NaOH, H2O and brine
  2. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-12afe95e839b42e0a1b45d0d17319974
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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