Chloroacetyl chloride → Chloroacetic acid morpholine carboxamide

HRID 2703

Reaction equation

HRID 2703 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 in vacuo 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 in vacuo

Sources & evidence

ORD record
ord-76b9fb90e765478eb9f07bde4c5ac1d8
Source dataset
uspto-grants-1998_03
Patent number
US05731306

Linked notes

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