Chloroacetyl chloride → HCID 53682946, compound

HRID 441035Notes

Reaction equation

HRID 441035 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[CH2:10][NH:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:13][CH2:14][C:15]([N:11]([OH:12])[CH2:10][C@@H:8]1[CH2:9][C@H:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:16]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 15550376HCID 15550376, compound

Product 1

HCID 53682946HCID 53682946, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-[(trans-2-phenylcyclopropyl)methyl]-N-hydroxylamine (3.26 g, 20 mM) in methylene chloride (50 ml) was added chloroacetyl chloride (4.52 g, 40 mM) and triethylamine (4.04 g, 40 ml) at room temperature. After stirring for 5 hours, it was poured into saturated aqueous sodium bicarbonate. The whole was extracted with chloroform (2×100 ml). The extracts were washed with water and brine, then were added and evaporated in vacuo. Chromatographic purification (eluent chloroform:ethanol=15:1) of the residue provided 2 g (41.8% yield) of the desired product as a pale yellow oil.

Workup

  1. extractionThe whole was extracted with chloroform (2×100 ml)
  2. washThe extracts were washed with water and brine
  3. additionwere added
  4. customevaporated in vacuo
  5. customChromatographic purification (eluent chloroform:ethanol=15:1) of the residue

Sources & evidence

ORD record
ord-e6d69225cbac423681d92f1ac0a08fcd
Source dataset
uspto-grants-1996_05
Patent number
US05521212

Reaction notes

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