Ethanol → HCID 21392597, compound

HRID 1580711Notes

Reaction equation

HRID 1580711 reaction equation
[CH2:1]([C:4]1[C:13]2[O:12][C:11]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)=[CH:10][C:9](=[O:19])[C:8]=2[C:7]([O:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[Na+].C(O)C>O>[CH2:1]([C:4]1[C:13]2[O:12][C:11]([C:14]3[N:15]([CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:16]=[N:17][N:18]=3)=[CH:10][C:9](=[O:19])[C:8]=2[C:7]([O:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:6][CH:5]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 178439275HCID 178439275, compound

Product 1

HCID 21392597HCID 21392597, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 parts of 5-[8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-yl]tetrazole, 16.6 parts of benzyl bromide, 3.53 parts of sodium hydroxide, 120 parts of ethanol and 60 parts of water was refluxed for 64 hours. The mixture was cooled, was extracted with chloroform and the chloroform extract washed with sodium bicarbonate solution and water. Evaporation of the chloroform gave a residue which was chromatographed in silica gel. Elution with 3 : 1 toluene/acetic acid and chloroform gave, after crystallisation from ethanol, a total of 7.31 parts of 5-[8-allyl-5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-yl]-N-benzyltetrazole, m.p. 92.5°-94°C.

Workup

  1. temperaturewas refluxed for 64 hours
  2. temperatureThe mixture was cooled
  3. extractionwas extracted with chloroform
  4. extractionthe chloroform extract
  5. washwashed with sodium bicarbonate solution and water
  6. customEvaporation of the chloroform
  7. customgave a residue which
  8. customwas chromatographed in silica gel
  9. washElution with 3 : 1 toluene/acetic acid and chloroform
  10. customgave
  11. customafter crystallisation from ethanol

Sources & evidence

ORD record
ord-f788626c719b4017ae41634f239a4500
Source dataset
uspto-grants-1976_01
Patent number
US03933845

Reaction notes

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