Hydrochloric Acid → HCID 178435517, compound

HRID 2211394Notes

Reaction equation

HRID 2211394 reaction equation
[C:1]1([CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[C:20]([O:22]CC3C=CC=CC=3)[C:19]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:18][C:17]=2[CH2:37][CH3:38])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:39]=[N+:40]=[N-:41].[Na+].Cl.C(N(CC)CC)C.Cl>CN(C)C=O>[C:1]1([CH:7]([C:8]2[NH:9][N:41]=[N:40][N:39]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[C:20]([OH:22])[C:19]([C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[CH:18][C:17]=2[CH2:37][CH3:38])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 19375780HCID 19375780, compound

Product 1

HCID 178435517HCID 178435517, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

2-Phenyl-7-(2-ethyl-4-(4-fluorophenyl)-5-benzyloxyphenoxy)heptanenitrile (700 mg, 1.38 mmol) was dissolved in dimethylformamide (20 mL) and sodium azide (0.6 g) and triethylamine hydrochloride added (1.2 g) and the stirred suspension heated at 110° C. for 3 days. The suspension was then added to 1M hydrochloric acid (100 mL) and the solution extracted 4 times with chloroform. The combined chloroform extracts were washed with water and dried with magnesium sulfate. On evaporation the solution yielded 680 mg (72%) of the title compound as a crude oil which was then directly deprotected.

Workup

  1. extractionthe solution extracted 4 times with chloroform
  2. washThe combined chloroform extracts were washed with water
  3. dry with materialdried with magnesium sulfate
  4. customOn evaporation the solution

Sources & evidence

ORD record
ord-dea64f1b0ccf4d75b98bb5a486211540
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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