Methyl iodide → HCID 178504056, compound

HRID 1763555Notes

Reaction equation

HRID 1763555 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH:11][C:12]([NH2:14])=[S:13])[CH2:6][CH2:5]2.[CH3:15][I:16]>CO>[IH:16].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH:11][C:12](=[NH:14])[S:13][CH3:15])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 203105831-(5-Chloroindolin-1-yl)-thiourea

Product 1

HCID 178504056HCID 178504056, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-amino-5-chlorindoline was reacted with benzoyl isothiocyanate in boiling tetrahydrofuran. Saponification of the resulting product with dilute aqueous sodium hydroxide under reflux for 15 minutes gave 1-(5-chloroindolin-1-yl)-thiourea (M.Pt. 199° - 200° from ethyl acetate/petroleum ether). This thiourea was heated in boiling methanol in the presence of methyliodide for 1 hour to give 1-(5-chloroindolin-1-yl)-2-methylisothiourea hydroiodide. The base was liberated with aqueous sodium hydroxide. Reaction of the base with 2N ethanolic hydrogen chloride yielded 1-(5-chlorindolin-1-yl)-2-methylisothiourea hydrochloride (M.Pt. 178° - 179° from ethanol/ether).

Workup

  1. customfor 1 hour

Sources & evidence

ORD record
ord-2674ed73938f462bb6d63002d8159707
Source dataset
uspto-grants-1978_09
Patent number
US04112111

Reaction notes

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