Hydrochloric Acid → HCID 178492480, compound

HRID 389299Notes

Reaction equation

HRID 389299 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:12][C:13]2[C:14]([CH3:22])=[N:15][N:16]([CH2:19][C:20]#[N:21])[C:17]=2[CH3:18])=[C:7]2[C:11]=1[CH2:10][CH2:9][CH2:8]2.[N-:23]=[N+:24]=[N-:25].[Na+].Cl.C(N(CC)CC)C.Cl>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:12][C:13]2[C:14]([CH3:22])=[N:15][N:16]([CH2:19][C:20]3[NH:25][N:24]=[N:23][N:21]=3)[C:17]=2[CH3:18])=[C:7]2[C:11]=1[CH2:10][CH2:9][CH2:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 66812818HCID 66812818, compound

Product 1

HCID 178492480HCID 178492480, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of [4-(7-Methoxy-indan-4-yloxy)-3,5-dimethyl-pyrazol-1-yl]-acetonitrile (3.0 gm, 0.0101 mole) in Dimethylformamide (30 ml), Sodium azide (1.2 gm, 0.0185 mole) and Triethylamine hydrochloride (4.0 gm, 0.0303 mole) were added at room temperature (27-30° C.). The reaction mixture was stirred at 90-100° C. for 4 hours. The reaction mixture was cooled and poured into dilute Hydrochloric acid (100 ml) and stirred for 30 minutes. The separated solid was filtered and dissolved in Ethyl acetate (100 ml). The Ethyl acetate layer was dried over Sodium sulphate and distilled under vacuum to get a 1.5 gm of desired product as a solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. stirringstirred for 30 minutes
  3. filtrationThe separated solid was filtered
  4. dissolutiondissolved in Ethyl acetate (100 ml)
  5. dry with materialThe Ethyl acetate layer was dried over Sodium sulphate
  6. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-dd8aac49ce5043f490cf90e0c3ee82e9
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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