Ammonium Chloride → HCID 178508507, compound

HRID 1195061Notes

Reaction equation

HRID 1195061 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][C:16]#[N:17])/[C:8]([O:10]CC)=[O:9])[N:6]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+]>CN(C)C=O.O.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][C:16]2[NH:17][N:20]=[N:19][N:18]=2)/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 88630612ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(cyanomethoxyimino)acetate

Product 1

HCID 178508507HCID 178508507, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

5.0 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetate are heated to 60° C. for 48 hours while stirring together with 1.95 g of sodium azide and 1.6 g of ammonium chloride in 50 ml of dimethylformamide. The mixture is taken up in water/ethyl acetate. The ethyl acetate phase is washed twice with a small amount of water. The combined aqueous phases are concentrated to dryness, the residue is dissolved in 50 ml of 1N aqueous sodium hydroxide solution and stored at room temperature for 1 hour. The mixture is subsequently diluted with 50 ml of water and the solution is concentrated to 50 ml. The product crystallizes after the addition of 50 ml of aqueous 1N hydrochloric acid. There are obtained 3.9 g of 2-(2-amino-4-thiazolyl)-2-[(Z)-(1H-tetrazol-5-yl-methoxy)imino]-acetic acid of melting point 151°-152° C. The water content is 6.96%.

Workup

  1. washThe ethyl acetate phase is washed twice with a small amount of water
  2. concentrationThe combined aqueous phases are concentrated to dryness
  3. dissolutionthe residue is dissolved in 50 ml of 1N aqueous sodium hydroxide solution
  4. additionThe mixture is subsequently diluted with 50 ml of water
  5. concentrationthe solution is concentrated to 50 ml
  6. customThe product crystallizes
  7. additionafter the addition of 50 ml of aqueous 1N hydrochloric acid

Sources & evidence

ORD record
ord-47b6c02d41824f458d4486228845547b
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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