Hydrogen Bromide → HCID 178439264, compound

HRID 461834Notes

Reaction equation

HRID 461834 reaction equation
CC(C)CC[O:5][C:6]1[C:11]2[C:12](=[O:21])[CH:13]=[C:14]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[O:15][C:10]=2[C:9]([CH2:22][CH2:23][CH3:24])=[CH:8][CH:7]=1.Br.C(=O)(O)[O-].[Na+].Cl>O>[OH:5][C:6]1[C:11]2[C:12](=[O:21])[CH:13]=[C:14]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[O:15][C:10]=2[C:9]([CH2:22][CH2:23][CH3:24])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178439276HCID 178439276, compound

Product 1

HCID 178439264HCID 178439264, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 parts of 5-[5-(3-methyl-n-butoxy)-8-n-propyl-4-oxo-4H-1 -benzopyran-2-yl]tetrazole in 130 parts by volume of 48% aqueous hydrobromic acid was refluxed for 3 hours, then cooled and water added. The resulting mixture was neutralised by the addition of solid sodium bicarbonate, then made slightly acidic by re-acidification with dilute hydrochloric acid and extracted with chloroform. The chloroform extract was washed with saturated brine and water, and was dried. Evaporation of the chloroform gave a solid which was purified by precipitation from aqueous ethanol to give 0.36 parts of 5-[5-hydroxy-8-n-propyl-4-oxo-4H-1-benzopyran-2-yl]tetrazole, m.p. 242.5°-245° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturecooled
  3. extractionextracted with chloroform
  4. extractionThe chloroform extract
  5. washwas washed with saturated brine and water
  6. customwas dried
  7. customEvaporation of the chloroform
  8. customgave a solid which
  9. customwas purified by precipitation from aqueous ethanol

Sources & evidence

ORD record
ord-661bce5a661d4a11a8b1cdfca3d92066
Source dataset
uspto-grants-1977_12
Patent number
US04064256

Reaction notes

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