Sodium Iodide → HCID 21269044, compound

HRID 1195068Notes

Reaction equation

HRID 1195068 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.[CH2:15]([N:17]([CH2:22][CH3:23])[C:18](=[O:21])[CH2:19]Cl)[CH3:16].C(N(C(C)C)C(C)C)C.[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][CH2:19][C:18](=[O:21])[N:17]([CH2:22][CH3:23])[CH2:15][CH3:16])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 16844Chloro-N,N-diethylacetamideHCID 81531DiisopropylethylamineHCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Product 1

HCID 21269044HCID 21269044, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

57.3 g of ethyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate, 80 g of N,N-diethylchloroacetamide, 138.7 ml of N-ethyldiisopropylamine and 80 g of sodium iodide are stirred at room temperature for 12 hours in 1.1 l of acetonitrile. The mixture is subsequently diluted with 5 l of ethyl acetate, washed with water, dried over magnesium sulphate and concentrated to a small volume. The compound which crystallizes out is filtered off and dried. There are obtained 68.1 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-[(diethylcarbamoyl)methoxy]imino]-acetate of melting point 161° C.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to a small volume
  4. customThe compound which crystallizes out
  5. filtrationis filtered off
  6. customdried

Sources & evidence

ORD record
ord-6cb0964894624f7cbf5700f886139c2e
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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