Sodium Iodide → HCID 21269047, compound

HRID 1195064Notes

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]([CH:21]([CH3:23])C)[CH:18]([CH3:20])C)[CH3:16].[I-].[Na+].C(OCC)(=[O:28])C.[C:32](#N)[CH3:33]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:23][C:21]([N:17]2[CH2:15][CH2:16][CH2:33][CH2:32][CH2:20][CH2:18]2)=[O:28])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

Reactant 5

HCID 5238Sodium Iodide

HCID 6342Acetonitrile

HCID 8857Ethyl Acetate

HCID 81531Diisopropylethylamine

HCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Product 1

HCID 21269047HCID 21269047, compound

Procedure

99 g of ethyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate, 121.4 g of N-chloroacetylhexamethyleneimine, 238 ml of N-ethyldiisopropylamine and 103.5 g of sodium iodide are stirred at room temperature for 12 hours in 1675 ml of acetonitrile. The mixture is poured into 7 l of ethyl acetate, washed with water, dried over magnesium sulphate and concentrated. After recrystallization from isopropyl acetate, there are obtained 136 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-[[(hexahydro-1H-azepin-1-yl)carbonyl]methoxy]imino]-acetate of melting point 163°-164° C.

Workup

washwashed with water
dry with materialdried over magnesium sulphate
concentrationconcentrated
customAfter recrystallization from isopropyl acetate, there

Sources & evidence

ORD record: ord-94a806f1dc264cce9d059faceb126160
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04816582

Reaction notes

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