Chloroacetyl chloride → Chloroacetic acid morpholine carboxamide

HRID 1289416

Reaction equation

HRID 1289416 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C[N:7]1CC[O:10]CC1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>ClCCl>[N:13]1([C:3]([NH2:7])=[O:4])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[Cl:1][CH2:2][C:3]([OH:4])=[O:10]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 79724-MethylmorpholineHCID 8083Morpholine

Product 1

HCID 88103447Chloroacetic acid morpholine carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine chloroacetyl chloride (2.00 mL, 25.0 mmol) and N-methylmorpholine (2.76 mL, 25.0 mmol) in dichloromethane (100 mL). Cool in an ice-bath. Add morpholine (2.19 mL, 25.0 mmol) and stir in the ice-bath for 1 hour. Warm to ambient temperature and stir for 1 hour. Extract with cold aqueous 5% sulfuric acid solution, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate invacuo to obtain chloroacetic acid morpholine carboxamide.

Workup

  1. temperatureCool in an ice-bath
  2. extractionExtract with cold aqueous 5% sulfuric acid solution, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate invacuo

Sources & evidence

ORD record
ord-d43abefa04ed4285b98b38b72f6092c2
Source dataset
uspto-grants-1998_05
Patent number
US05750521

Linked notes

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