Bis(S-methylisothiouronium) sulfate → HCID 12044047, compound

HRID 1840541Notes

Reaction equation

HRID 1840541 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[C:18](=[O:30])[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.S(O)(O)(=O)=O.CS[C:38](=[NH:40])[NH2:39].CSC(=N)N.C[O-].[Na+]>CO>[C:38]([N:27]1[CH2:28][CH2:29][CH:24]([CH2:23][CH2:22][N:19]2[CH2:20][CH2:21][N:16]([S:13]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][CH:12]=[C:3]([Cl:2])[CH:4]=4)[CH:9]=3)(=[O:15])=[O:14])[CH2:17][C:18]2=[O:30])[CH2:25][CH2:26]1)(=[NH:39])[NH2:40]

Participants

5

Reactant 3

HCID 13347Bis(S-methylisothiouronium) sulfateHCID 10942334Sodium MethoxideHCID 23447545HCID 23447545, compound

Product 1

HCID 12044047HCID 12044047, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-(6-chloronaphthalene-2-sulfonyl)-1-[2-(4-piperidyl)ethyl]-2-piperazinone Hydrochloride (118 mg) in methanol (10 ml) was added a solution of S-methylisothiourea hemisulfate (315 mg) and 28% sodium methoxide in methanol (482 mg), and the mixture was stirred at room temperature for 3 days. The solvent was concentrated and purified with CHP20 column chromatography (water:acetonitrile:1 N hydrochloric acid=70:30:1), and then purified with LH20 (methanol) to give colorless amorphous of the title compound (66 mg).

Workup

  1. concentrationThe solvent was concentrated
  2. custompurified with CHP20 column chromatography (water:acetonitrile:1 N hydrochloric acid=70:30:1)
  3. custompurified with LH20 (methanol)

Sources & evidence

ORD record
ord-7b5f273cdd714c71bd2a7b57c4e8ccba
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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