Methylthiourea → 8b-hydroxy-2-(methylamino)-3a,4-dihydroindeno[1,2-d][1,3]thiazole-6-carbonitrile;hydrobromide

HRID 1977818Notes

Reaction equation

HRID 1977818 reaction equation
[Br:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[C:3]1=[O:13].[CH3:14][NH:15][C:16]([NH2:18])=[S:17]>CC(C)=O>[BrH:1].[OH:13][C:3]12[C:4]3[CH:5]=[CH:6][C:7]([C:11]#[N:12])=[CH:8][C:9]=3[CH2:10][CH:2]1[S:17][C:16]([NH:15][CH3:14])=[N:18]2.[OH:13][C:3]12[C:4]3[CH:5]=[CH:6][C:7]([C:11]#[N:12])=[CH:8][C:9]=3[CH2:10][CH:2]1[S:17][C:16]([NH:15][CH3:14])=[N:18]2

Participants

5

Reactant 2

HCID 2723704MethylthioureaHCID 184072382-Bromo-1-oxoindan-5-carbonitrile

Product 2

HCID 1784195908b-hydroxy-2-(methylamino)-3a,4-dihydroindeno[1,2-d][1,3]thiazole-6-carbonitrile;hydrobromideHCID 1784823398b-hydroxy-2-(methylamino)-3a,4-dihydroindeno[1,2-d][1,3]thiazole-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

236 mg of 2-bromo-1-oxoindane-5-carbonitrile are dissolved in 10 ml of acetone and, at 0° C., 135 mg of N-methylthiourea are added. The mixture is stirred at room temperature for 3 h and at ice-bath temperature for 90 minutes. The precipitate is filtered off with suction, washed with acetone and dried in vacuo. The hydrobromide of 3a-hydroxy-2-methylamino-8,8a-dihydro-3aH-indeno[1,2-d]thiazole-6-carbonitrile is obtained with a melting point of 287-288° C.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. washwashed with acetone
  3. customdried in vacuo

Sources & evidence

ORD record
ord-07d4b75b0cf1426b8076f4cd7b087752
Source dataset
uspto-grants-2001_05
Patent number
US06235763B1

Reaction notes

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