Methanol → (+)-N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide

HRID 1789362Notes

Reaction equation

HRID 1789362 reaction equation
[CH3:1][N:2](C(C1CCCN1S(C1C=CC2C(=CC=CC=2)C=1)(=O)=O)=O)[C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[S:4].O1CCCC1.CO.[OH-].[Na+]>O>[CH3:1][NH:2][C:3]([N:5]1[CH2:9][CH2:8][S:7][CH:6]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:23][CH2:24]1)=[S:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 13808972(-)-N-methyl-N-[1-(2-naphthylsulfonyl)pyrrolidine-2-carbonyl]-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide

Product 1

HCID 13767979(+)-N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamideYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.05 g of (-)-N-methyl-N-[1-(2-naphthylsulfonyl)pyrrolidine-2-carbonyl]-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide, 40 ml of tetrahydrofuran, 40 ml of methanol, 120 mg of sodium hydroxide and 3 ml of water are treated in the same manner as described in Example 148-(2). 600 mg of (-)-N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carbothioamide are obtained. Yield: 94.2%.

Sources & evidence

ORD record
ord-63d52bf819e7416a9fcd3ec481ab9c00
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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