HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Chloroacetyl chloride → 2-chloro-N-(5-chloropyridin-2-yl)acetamide

HRID 16701
Notes
Print preview

Reaction equation

HRID 16701 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.C(N(CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 661742-Amino-5-chloropyridine

Product 1

HCID 51511482-chloro-N-(5-chloropyridin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloroacetyl chloride (95.5 ml) is dissolved in dichloromethane (500 ml), and thereto is added dropwise a suspension of 2-amino-5-chloropyridine (128.6 g) and triethylamine (169 ml) in dichloromethane (1000 ml) under ice-cooling. The reaction solution is warmed to room temperature and stirred for 0.5 hours. The reaction solution is concentrated under reduced pressure, and thereto is poured ice-water, followed by extraction with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and treated with activated charcoal. After filtration to remove insoluble materials, the filtrate is concentrated under reduced pressure and the resulting residue is suspended in diisopropyl ether. The precipitates are collected by filtration, washed with diisopropyl ether and dried to give the title compound (153.4 g).

Workup

  1. additionis added dropwise
  2. temperaturecooling
  3. concentrationThe reaction solution is concentrated under reduced pressure
  4. additionis poured ice-water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer is washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. additiontreated with activated charcoal
  9. filtrationAfter filtration
  10. customto remove insoluble materials
  11. concentrationthe filtrate is concentrated under reduced pressure
  12. filtrationThe precipitates are collected by filtration
  13. washwashed with diisopropyl ether
  14. customdried

Sources & evidence

ORD record
ord-2e3c107286284bc597d69ee46a2d4bb6
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737161B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes