Sodium Iodide → HCID 21269052, compound

HRID 1195066Notes

Reaction equation

HRID 1195066 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[OH:14])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.C(N(C(C)C)C(C)C)C.Cl[CH2:25][C:26]1[N:30]([CH3:31])[N:29]=[N:28][N:27]=1.[I-].[Na+]>C(#N)C.C(OCC)(=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:25][C:26]2[N:30]([CH3:31])[N:29]=[N:28][N:27]=2)/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetateHCID 122050865-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazole

Product 1

HCID 21269052HCID 21269052, compoundYield 154.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

17.7 g of ethyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate are suspended in 320 ml of acetonitrile, treated successively with 27.6 ml of N-ethyldiisopropylamine, 16 g of 5-chloromethyl-1-methyl-tetrazole and 24 g of sodium iodide and the mixture is stirred at room temperature for 12 hours. The mixture is subsequently diluted with 1.5 l of ethyl acetate, washed three times with 500 ml of water each time, dried over magnesium sulphate and concentrated. There are obtained 39.6 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-[(1-methyl-1H-tetrazol-5-yl)methoxy]imino]-acetate as an oil which is used directly.

Workup

  1. washwashed three times with 500 ml of water each time
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-15b8d17e59694e27906ea1717ed8baa5
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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