Hydrochloric Acid → HCID 178419943, compound

HRID 1421932Notes

Reaction equation

HRID 1421932 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]#[N:13].[Cl-].[NH4+].[N-:16]=[N+:17]=[N-:18].[Na+].Cl>CN(C=O)C.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[NH:18][N:17]=[N:16][N:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 820082-Naphthylacetonitrile

Product 1

HCID 178419943HCID 178419943, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of the above acetonitrile (2.50 g, 15 mmol), ammonium chloride (1.60 g, 30 mmol) and sodium azide (1.94 g, 30 mmol) in N,N'-dimethylformamide (25 ml) was stirred at 125° C. for 15 hours. The cooled reaction mixture was poured into water (300 ml) and acidified with 1 N hydrochloric acid, stirred at room temperature for 2 hours. The precipitate was filtered off and washed successively with water, a 1:1 mixture of diethyl ether and heptane and finally with heptane. The solid was dried by suction affording 1.69 g (53%) of the title compound as a solid.

Workup

  1. customThe cooled reaction mixture
  2. stirringstirred at room temperature for 2 hours
  3. filtrationThe precipitate was filtered off
  4. washwashed successively with water
  5. additiona 1:1 mixture of diethyl ether and heptane
  6. customThe solid was dried by suction

Sources & evidence

ORD record
ord-b41af90bf0104980b4ba25a27b409cc5
Source dataset
uspto-grants-2000_06
Patent number
US06080770

Reaction notes

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