Sodium Hydroxide → 1-(5-Chloroindolin-1-yl)-thiourea

HRID 1763554Notes

Reaction equation

HRID 1763554 reaction equation
[NH2:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.C([N:20]=[C:21]=[S:22])(=O)C1C=CC=CC=1.[OH-].[Na+]>O1CCCC1>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([NH:1][C:21]([NH2:20])=[S:22])[CH2:3][CH2:4]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 68284Benzoyl isothiocyanateHCID 203105795-Chloro-n-aminoindoline

Product 1

HCID 203105831-(5-Chloroindolin-1-yl)-thiourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Sources & evidence

ORD record
ord-85f19557af274f5f8ea82fbe6472eef6
Source dataset
uspto-grants-1978_09
Patent number
US04112111

Reaction notes

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