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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 443478Generated: October 25, 2026

Bis(S-methylisothiouronium) sulfate → 2-Guanidinomethyl-indoline hemisulphate

https://huagongshe.com/reaction/443478

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBis(S-methylisothiouronium) sulfateHCID 13347—
ReactantThionyl ChlorideHCID 24386—
ReactantEthyl Indoline-2-carboxylateHCID 11949691—
Reactant1-Benzyl-2-chloromethyl-indolineHCID 23467351—
ReactantPhthalimide potassium saltHCID 24194345—
Reactant1-Benzyl-2-guanidinomethyl-indoline hemisulphateHCID 178512742—
CatalystPalladiumHCID 23938—
SolventEthanolHCID 702—
Product2-Guanidinomethyl-indoline hemisulphateHCID 178512743—

Reaction Steps

10 g of 1-benzyl-2-guanidinomethyl-indoline hemisulphate (obtainable from ethyl indoline-2-carboxylate by N-benzylation, reduction and reaction with SOCl2 to give 1-benzyl-2-chloromethyl-indoline, reaction of the latter with potassium phthalimide and hydrolysis of the reaction product, and reaction of this product with S-methyl-isothiourea hemisulphate) are dissolved in 200 ml of ethanol and hydrogenated over 3 g of 5% Pd/C at 20° C. and 1 atmosphere until the reaction ceases. After filtering and evaporating the filtrate, 2-guanidinomethyl-indoline hemisulphate is obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04260628
Source datasetuspto-grants-1981_04
ORD IDord-fba2e1b2f2a44d9c9008b938e3f3152c
Source noteuspto-grants-1981_04