Water → HCID 178419937, compound

HRID 1741161Notes

Reaction equation

HRID 1741161 reaction equation
[C:1]1([CH2:11][C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+].[N-:16]=[N+:17]=[N-:18].[Na+].O>CN(C=O)C>[C:1]1([CH2:11][C:12]2[NH:18][N:17]=[N:16][N:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 85961-NaphthaleneacetonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 178419937HCID 178419937, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of the above acetonitrile (5.40 g, 32 mmol), ammonium chloride (2.59 g, 48 mmol) and sodium azide (3.15 g, 48 mmol) in N,N'-dimethylformamide (100 ml) was stirred at 125° C. for 16 hours. After cooling the mixture was poured into water (300 ml) and extracted with ethyl acetate (2×150 ml) The combined organic phases were washed with water (100 ml) and evaporated in vacua. The residue was crystallised from diethyl ether (20 ml), filtered off and washed with diethyl ether affording 1.86 g (27%) of the title compound as a solid.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate (2×150 ml) The combined organic phases
  3. washwere washed with water (100 ml)
  4. customevaporated in vacua
  5. customThe residue was crystallised from diethyl ether (20 ml)
  6. filtrationfiltered off
  7. washwashed with diethyl ether affording 1.86 g (27%) of the title compound as a solid

Sources & evidence

ORD record
ord-ad33406dfdb44141b45c0e9d4f51caac
Source dataset
uspto-grants-1999_10
Patent number
US05972978

Reaction notes

Loading…