Diisopropyl Ether → Ethyl thiazole-4-carboxylate

HRID 1531400Notes

Reaction equation

HRID 1531400 reaction equation
COC1C=C(OC)C(OC)=CC=1C(N[C:8]1[S:9][CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:12]=1)=O.C(N(C(C)C)CCNC)(C)C.S([O-])(O)(=O)=O.[K+].C(OC(C)C)(C)C>CC(N(C)C)=O.C(OCC)(=O)C>[CH2:16]([O:15][C:13]([C:11]1[N:12]=[CH:8][S:9][CH:10]=1)=[O:14])[CH3:17]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 516920Potassium bisulfateHCID 10215672Ethyl 2-(2,4,5-trimethoxybenzamido)thiazole-4-carboxylateHCID 14979281{2-[Bis(propan-2-yl)amino]ethyl}(methyl)amine

Product 1

HCID 5003096Ethyl thiazole-4-carboxylateYield 86%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

A suspension (1.5 ml) of 2-[N-(2,4,5-trimethoxybenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazole (732 mg) and N,N-diisopropyl-N′-methylethylenediamine (1.60 g) in dimethylacetamide was stirred at 140° C. for 5 hours. To the reaction mixture, an aqueous solution of potassium hydrogensulfate, a small quantity of ethyl acetate, and a small quantity of isopropyl ether were added for precipitation of crystals. Crystals so precipitated were collected by filtration and dried to thereby obtain 601 mg of 2-[N-4,5-dimethoxy-2-hydroxybenzoyl)amino]-4-(ethoxycarbonyl)-1,3-thiazole (yield: 86%).

Workup

  1. customCrystals so precipitated
  2. filtrationwere collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-06ef2abc228440ea833526d750d89309
Source dataset
uspto-grants-2001_03
Patent number
US06197970B1

Reaction notes

Loading…