1,2-Dichloroethane → HCID 18768988, compound

HRID 480243Notes

Reaction equation

HRID 480243 reaction equation
Cl.[CH2:2]([N:9]([CH2:11][C:12]([OH:14])=O)[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(Cl)CCl.Cl.[CH3:20][NH:21][O:22][CH3:23].CN1CCOCC1>CN(C=O)C>[CH2:2]([N:9]([CH3:10])[CH2:11][C:12]([N:21]([O:22][CH3:23])[CH3:20])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 457924962-(Benzyl(methyl)amino)acetic acid hydrochloride

Product 1

HCID 18768988HCID 18768988, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Benzyl-methyl-amino)-acetic acid hydrochloride salt (12 g, 56 mmol, 1.0 equiv) was mixed in DMF (200 mL) along with EDC (10.6 g, 56 mmol, 1.0 equiv) for 15 min. N,O-Dimethylhydroxylamine hydrochloride (6.52 g, 67 mmol, 1.2 equiv) was added to the reaction followed by N-methylmorpholine (34 mL, 334 mmol, 6.0 equiv). The reaction was stirred for 16 h. The DMF was removed in vacuo and the residue was redissolved in 200 mL of EtOAc. The solution was washed once with 200 mL brine. The organic layer was dried over Na2SO4, decanted and concentrated to yield the desired product as a free-flowing oil (12.6 g, 80%) that was used in the next step without further purification; MS, m/z 223=M+1.

Workup

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue was redissolved in 200 mL of EtOAc
  3. washThe solution was washed once with 200 mL brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8410779ee1ba479086877a6f0b6e9fb8
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Reaction notes

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