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Sodium Azide → ethyl 7-(azidomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854892
Notes
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Reaction equation

HRID 854892 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]([C:13]([F:16])([F:15])[F:14])[O:10]2)=[CH:5][C:4]=1[Cl:22].[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C>[N:23]([CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]([C:13]([F:16])([F:15])[F:14])[O:10]2)=[CH:5][C:4]=1[Cl:22])=[N+:24]=[N-:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 69517129ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 86599453ethyl 7-(azidomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The ester from step 3 (2.2 g, 5.5 mmole) and sodium azide (1.79 g, 27.5 mmole) were dissolved in DMF (15 mL). The mixture was heated at 50° C. under nitrogen for overnight. The solid was filtered off and washed with EtOAc. The organic layer was washed with water and dried over MgSO4. After concentrated the ester was of suitable purity to use without further purification.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentrated the ester
  6. customto use without further purification

Sources & evidence

ORD record
ord-68abea5559674609b1cc094c96b3f093
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259266B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes