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Dimethylformamide → 5-[2-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]ethyl]-1H-tetrazole

HRID 1048
Notes
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Reaction equation

HRID 1048 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[N:17]=[C:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:19][C:20]=3[CH3:21])[CH:11]=[CH:10][C:8]=2[CH:9]=1)#[N:2].[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+].CN(C)C=O>O>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:17][C:16]=1[CH2:15][O:14][C:12]1[CH:11]=[CH:10][C:8]2[CH:9]=[C:5]([CH2:4][CH2:3][C:1]3[NH:30][N:29]=[N:28][N:2]=3)[O:6][C:7]=2[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 101553132-(2-Cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran

Product 1

HCID 1784184515-[2-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]ethyl]-1H-tetrazoleYield 78.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran (1.20 g), sodium azide (1.09 g), ammonium chloride (0.90 g) and N,N-dimethylformamide (30 ml) was stirred at 130° to 140° C. for 16 hours. The reaction mixture was poured over water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; the residue was subjected to silica gel column chromatography. From the fraction eluted with methanol-chloroform (5:95, v/v), 5-[2-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]ethyl ]-1H-tetrazole (1.05 g, 78%) was obtained, which was then recrystallized from dichloromethane-methanol to yield colorless prisms having a melting point of 177° to 178° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off
  5. washFrom the fraction eluted with methanol-chloroform (5:95

Sources & evidence

ORD record
ord-2e59b47848294fe195989e641f0b30fb
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723479

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes