3-Pyridylthiourea → 3-Nitro-5-[2-(3-pyridylamino)-4-thiazolyl]pyrocatechol hydrobromide

HRID 725348Notes

Reaction equation

HRID 725348 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[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([NH2:25])=[S:24])[CH:17]=1>C(O)CCC>[BrH:1].[N+:11]([C:9]1[CH:10]=[C:5]([C:3]2[N:25]=[C:23]([NH:22][C:18]3[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=3)[S:24][CH:2]=2)[CH:6]=[C:7]([OH:15])[C:8]=1[OH:14])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 27605153-PyridylthioureaHCID 218455962-Bromo-1-(3,4-dihydroxy-5-nitro-phenyl)-ethanone

Product 1

HCID 214590513-Nitro-5-[2-(3-pyridylamino)-4-thiazolyl]pyrocatechol hydrobromide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 7.32 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 4.06 g of 1-(3-pyridinyl)-2-thiourea in 100 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-pyridylamino)-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-3a3d6193bd2f402c955db59fa633272a
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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