(Quinolin-3-yl)thiourea → 3-Nitro-5-[2-(3-quinolinylamino)-4-thiazolyl]pyrocatechol hydrobromide

HRID 725349Notes

Reaction equation

HRID 725349 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([OH:14])=[C:7]([OH:15])[CH:6]=1)=O.[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([NH:26][C:27]([NH2:29])=[S:28])[CH:17]=1>C(O)CCC>[BrH:1].[N+:11]([C:9]1[CH:10]=[C:5]([C:3]2[N:29]=[C:27]([NH:26][C:18]3[CH:17]=[N:16][C:25]4[C:20]([CH:19]=3)=[CH:21][CH:22]=[CH:23][CH:24]=4)[S:28][CH:2]=2)[CH:6]=[C:7]([OH:15])[C:8]=1[OH:14])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 1480927(Quinolin-3-yl)thioureaHCID 218455962-Bromo-1-(3,4-dihydroxy-5-nitro-phenyl)-ethanone

Product 1

HCID 214590833-Nitro-5-[2-(3-quinolinylamino)-4-thiazolyl]pyrocatechol hydrobromide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 6.35 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 4.68 g of 1-(3-quinolinyl)-2-thiourea in 150 ml of n-butanol and heated to boiling under reflux for 3 hours. After cooling to room temperature the crystals are filtered under suction and recrystallized from n-butanol. There is obtained 3-nitro-5-[2-(3-quinolinylamino)-4-thiazolyl]pyrocatechol hydrobromide of m.p. >300°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. filtrationare filtered under suction
  4. customrecrystallized from n-butanol

Sources & evidence

ORD record
ord-9c78f62dcf044621b10dfe48d218705c
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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