Sodium Iodide → HCID 21269051, compound

HRID 1195062Notes

Reaction equation

HRID 1195062 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.Cl[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18].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][CH2:16][C:17]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 2223122-Chloro-1-piperidine-1-yl-ethanoneHCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Product 1

HCID 21269051HCID 21269051, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

83.8 g of ethyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate, 94.4 g of N-chloroacetylpiperidine, 202.5 ml of N-ethyldiisopropylamine and 87.6 g of sodium iodide are stirred at room temperature for 12 hours in 1420 ml of acetonitrile. The mixture is diluted with 7 l of ethyl acetate, washed with water, dried over magnesium sulphate and concentrated to a small volume. The substance which crystallizes ot is filtered off and dried. There are obtained 77.2 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-[(1-piperidinecarbonyl)methoxy]imino]-acetate of melting point 151°-152° C.

Workup

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

Sources & evidence

ORD record
ord-29f866ec59db47e6a4ae6b9011f4e6c5
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

Loading…