2-Aminothiazole → HCID 54716315, compound

HRID 2232102Notes

Reaction equation

HRID 2232102 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[OH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][C:9]=1[C:24](OCC)=[O:25]>C1(C)C=CC=CC=1>[OH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][C:9]=1[C:24]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:25]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 85585358HCID 85585358, compound

Product 1

HCID 54716315HCID 54716315, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.08 g of 2-aminothiazole and 8.0 g of 1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxylic acid, ethyl ester in 250 ml of toluene was refluxed for 30 hours in a soxhlet apparatus containing 10 g of 4 Å molecular sieves. Evaporation of the volatiles afforded a residue which was purified by means of high pressure liquid chromatography (silica gel: 1:25 ethyl acetate-dichloromethane as the eluent). The resulant solution was degassed and evaporated. Recrystallization of the residue from diethyl ether yielded 6.35 g (67%) of 1,2-dihydro-4-hydroxy-1-phenyl-N-(2-thiazolyl)-3-quinolinecarboxamide, m.p. 220° C. (dec.).

Workup

  1. additioncontaining 10 g of 4 Å molecular sieves
  2. customEvaporation of the volatiles
  3. customafforded a residue which
  4. customwas purified by means of high pressure liquid chromatography (silica gel
  5. customThe resulant solution was degassed
  6. customevaporated
  7. customRecrystallization of the residue from diethyl ether

Sources & evidence

ORD record
ord-13d58314597e4d92a43af69a820f2b1a
Source dataset
uspto-grants-1988_11
Patent number
US04786644

Reaction notes

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