2-Aminothiazole → HCID 54716315, compound

HRID 1710060Notes

Reaction equation

HRID 1710060 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 4Å 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 resultant 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 4Å 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 resultant solution was degassed
  6. customevaporated
  7. customRecrystallization of the residue from diethyl ether

Sources & evidence

ORD record
ord-a93964049da84480a5f37ff805641c98
Source dataset
uspto-grants-1990_08
Patent number
US04952588

Reaction notes

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