Hydrochloric Acid → HCID 178478128, compound

HRID 486066Notes

Reaction equation

HRID 486066 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]#[N:19])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[NH:24][N:23]=[N:22][N:19]=4)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19097328HCID 19097328, compound

Product 1

HCID 178478128HCID 178478128, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (1-(4-Chlorobenzyl)indol-5-yl)oxyacetonitrile (2.0 g), sodium azide (0.55 g) and ammonium chloride (0.43 g) in N,N-dimethylformamide (15 ml) were heated at 140° C. for 5 hrs. The cooled mixture was poured into 5%-hydrochloride solution. The solution was extracted with ethyl acetate and the separated organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The crude product was recrystallized from ethanol to yield the titled product, m.p. 162°-163° C.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe separated organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-521e7f52e1844b4abaace95f795bc65c
Source dataset
uspto-grants-1994_03
Patent number
US05290788

Reaction notes

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