1-Adamantylthiourea → HCID 21459009, compound

HRID 725422Notes

Reaction equation

HRID 725422 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.[C:16]12([NH:26][C:27]([NH2:29])=[S:28])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2>C(O)CCC>[BrH:1].[C:16]12([NH:26][C:27]3[S:28][C:3]([C:5]4[CH:6]=[C:7]([OH:15])[C:8]([OH:14])=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=4)=[CH:2][N:29]=3)[CH2:25][CH:20]3[CH2:19][CH:18]([CH2:24][CH:22]([CH2:21]3)[CH2:23]1)[CH2:17]2

Participants

4

Reactant 2

HCID 7964291-AdamantylthioureaHCID 218455962-Bromo-1-(3,4-dihydroxy-5-nitro-phenyl)-ethanone

Product 1

HCID 21459009HCID 21459009, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 8.3 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 1-(1-adamantyl)-2-thiourea in 90 ml of n-butanol and the mixture is heated to boiling under reflux for 4 hours. After cooling to room temperature, the crystals are filtered under suction and recrystallized from n-butanol. There is obtained 5-[2-(1-adamantylamino)-5-thiazolyl]-3-nitropyrocatechol hydrobromide of m.p. 245°-247°.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. filtrationthe crystals are filtered under suction
  4. customrecrystallized from n-butanol

Sources & evidence

ORD record
ord-a319c79d912845249c833658d17f8070
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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