Ammonium Chloride → HCID 178424996, compound

HRID 1721848Notes

Reaction equation

HRID 1721848 reaction equation
[CH:1]1([N:6]([C:16]2[N:24]=[CH:23][N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3[CH2:25][CH2:26][CH2:27][CH2:28][C:29]#[N:30])[CH2:7][C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:31]=[N+:32]=[N-:33].[Na+].[Cl-:35].[NH4+]>CN(C)C=O>[ClH:35].[CH:1]1([N:6]([C:16]2[N:24]=[CH:23][N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][N:20]3[CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[NH:33][N:32]=[N:31][N:30]=2)[CH2:7][C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 20029973HCID 20029973, compound

Product 1

HCID 178424996HCID 178424996, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.8 g. (9.4 mmole) of the compound of Example 18, 1.9 g. sodium azide, 1.5 g. ammonium chloride and 30 ml. dimethylformamide is heated to 125° C. for 3 days. A further 1.2 g. sodium azide and 1.0 g. ammonium chloride are added thereto, stirring is continued for 6 hours at 125° C., the reaction mixture is cooled and evaporated and the residue is taken up in ethyl acetate, washed with water, extracted with 1N aqueous sodium hydroxide solution and the aqueous phase is acidified with hydrochloric acid. After extraction with dichloromethane, evaporation and trituration of the residue with diethyl ether, there is obtained 1.7 g. of the title compound (38% of theory); m.p. 140°-142° C.

Workup

  1. additionA mixture of 3.8 g
  2. temperaturethe reaction mixture is cooled
  3. customevaporated
  4. washwashed with water
  5. extractionextracted with 1N aqueous sodium hydroxide solution
  6. extractionAfter extraction
  7. customwith dichloromethane, evaporation and trituration of the residue with diethyl ether
  8. customthere is obtained 1.7 g

Sources & evidence

ORD record
ord-3b0a2fa6b9c543b09f69bd2aefb1c539
Source dataset
uspto-grants-1989_08
Patent number
US04853386

Reaction notes

Loading…