HCID 145805292, compound → HCID 154041583, compound

HRID 846911Notes

Reaction equation

HRID 846911 reaction equation
[N:1]([CH2:4][CH2:5][O:6]/[N:7]=[C:8](/[C:14]1[N:15]=[C:16]([NH:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:17][CH:18]=1)\[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][O:6]/[N:7]=[C:8](/[C:14]1[N:15]=[C:16]([NH:19][C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[S:17][CH:18]=1)\[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 1

HCID 145805292HCID 145805292, compound

Product 1

HCID 154041583HCID 154041583, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

16.4 g of 2-(tritylamino)-4-thiazoleglyoxylic acid ethyl ester (Z)-O-(2-azidoethyl) oxime were hydrogenated for 3.5 hours under normal pressure in 300 ml of methanol in the presence of 2.5 g of palladium/carbon (5%). The catalyst was filtered off and the solvent was removed in a vacuum. The residue was crystallized from carbon tetrachloride/petroleum ether (low-boiling). There was obtained 2-(tritylamino)-4-thiazoleglyoxylic acid ethyl ester (Z)-O-(2-aminoethyl) oxime as white crystals having a melting point of 126°-144° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed in a vacuum
  3. customThe residue was crystallized from carbon tetrachloride/petroleum ether (low-boiling)

Sources & evidence

ORD record
ord-c42c923b70e24dd186f767713befdc17
Source dataset
uspto-grants-1992_08
Patent number
US05138066

Reaction notes

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