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

Dimethylformamide → Ethyl 4-azido-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate

HRID 542121
Notes
Print preview

Reaction equation

HRID 542121 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7](Cl)[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.[N-:21]=[N+:22]=[N-:23].[Na+].CN(C=O)C>O>[N:21]([C:7]1[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=[C:3]([C:2]([F:20])([F:19])[F:1])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N+:22]=[N-:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

Product 1

HCID 13882885Ethyl 4-azido-2,6-bis(trifluoromethyl)-3-pyridinecarboxylateYield 83.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g (0.0155 mol) of product of Example 19, 1.0 g (0.0154 mol) of sodium azide and 20 ml of DMF was stirred for 1 hour and poured into 100 ml of water. The organic was extracted into 100 ml of CH2Cl2 which was washed with 50 ml of water and concentrated. The residue (6.0 g) was dissolved in 50 ml of petroleum ether then washed with 50 ml of water twice, dried (MgSO4) and concentrated to give a solid which was recrystallized from petroluem ether at low temperature to give 4.2 g (82%) of product as a light yellow solid; mp 63°-64.5° C.

Workup

  1. extractionThe organic was extracted into 100 ml of CH2Cl2 which
  2. washwas washed with 50 ml of water
  3. concentrationconcentrated
  4. dissolutionThe residue (6.0 g) was dissolved in 50 ml of petroleum ether
  5. washthen washed with 50 ml of water twice
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give a solid which
  9. customwas recrystallized from petroluem ether at low temperature

Sources & evidence

ORD record
ord-8564da8a4658472083faeaf0f75aaad7
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04655816

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes