Ammonium Chloride → HCID 178436666, compound

HRID 1608955Notes

Reaction equation

HRID 1608955 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[CH:21]=[CH:20][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]#[N:19])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>CN(C)C=O>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]3[NH:24][N:23]=[N:22][N:19]=3)=[CH:20][CH:21]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 54178215HCID 54178215, compound

Product 1

HCID 178436666HCID 178436666, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 5.3 g (19 mmol) of compound of Example 1, 3.7 g (57 mmol) sodium azide, 3.0 g (57 mmol) ammonium chloride and 40 ml N,N-dimethylformamide is stirred for 3 days at 125° C. One adds thereto a further 2.5 g sodium azide and 2.0 g ammonium chloride, stirs for a further 6 h at 125° C., evaporates, takes up the residue in water, extracts with dichloromethane, dries, evaporates and triturates with 2-propanol. There remain 2.7 g of title compound (44% of theory) of the m.p. 158°-159° C.

Workup

  1. additionOne adds
  2. customevaporates
  3. customevaporates

Sources & evidence

ORD record
ord-65d3572cb2e84207bf39f91aa3e978a0
Source dataset
uspto-grants-1995_03
Patent number
US05399575

Reaction notes

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