Hydrochloric Acid → HCID 178438982, compound

HRID 435863Notes

Reaction equation

HRID 435863 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23][CH2:24][CH3:25])=[CH:11][C:6]=2[O:5][C:4]([C:26]#[N:27])=[CH:3]1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23][CH2:24][CH3:25])=[CH:11][C:6]=2[O:5][C:4]([C:26]2[NH:30][N:29]=[N:28][N:27]=2)=[CH:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 130910034-Oxo-7-(3-[2-propylphenoxy]propoxy)-4H-1-benzopyran-2-carbonitrile

Product 1

HCID 178438982HCID 178438982, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 38.1 parts of 4-oxo-7-(3-[2-propylphenoxy]-propoxy)-4H-1-benzopyran-2-carbonitrile, 7.52 parts of sodium azide, 6.16 parts of ammonium chloride and 5,000 parts of dimethylformamide was stirred at 80° C for 15 hours. The reaction mixture was cooled and 2,000 parts of 2N hydrochloric acid were added to give a yellow solid which was collected. This product was dissolved in hot 3% sodium bicarbonate solution and the hot solution filtered and then cooled. The solid obtained was collected, washed with water and slurried with 500 parts of 2N hydrochloric acid. The resulting solid was collected, washed with water, dried and crystallised from acetone to give 18.4 parts of 5-(4-oxo-7-[3-{2-propylphenoxy}-propoxy]-4H-1-benzopyran-2-yl)-tetrazole m.pt. 191°-193°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customto give a yellow solid which
  3. customwas collected
  4. dissolutionThis product was dissolved in hot 3% sodium bicarbonate solution
  5. filtrationthe hot solution filtered
  6. temperaturecooled
  7. customThe solid obtained
  8. customwas collected
  9. washwashed with water
  10. customThe resulting solid was collected
  11. washwashed with water
  12. customdried
  13. customcrystallised from acetone

Sources & evidence

ORD record
ord-1d13211ba8974ed89e5301260437b7e0
Source dataset
uspto-grants-1977_02
Patent number
US04006245

Reaction notes

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