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

HRID 443478

Reaktionsgleichung

Reaktionsgleichung von HRID 443478
[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].C([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[CH2:22][NH:23][C:24]([NH2:26])=[NH:25])C1C=CC=CC=1.C(N1C2C(=CC=CC=2)CC1CNC(N)=N)C1C=CC=CC=1.N1C2C(=CC=CC=2)CC1C(OCC)=O.O=S(Cl)Cl.C(N1C2C(=CC=CC=2)CC1CCl)C1C=CC=CC=1.C1(=O)NC(=O)C2=CC=CC=C12.[K].S(O)(O)(=O)=O.CSC(=N)N.CSC(=N)N>C(O)C.[Pd]>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[NH:23]([CH2:22][CH:14]1[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:13]1)[C:24]([NH2:26])=[NH:25].[NH:23]([CH2:22][CH:14]1[CH2:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:13]1)[C:24]([NH2:26])=[NH:25]

Komponenten

9

Edukt 6

HCID 13347Bis(S-methylisothiouronium) sulfateHCID 24386Thionyl ChlorideHCID 11949691Ethyl Indoline-2-carboxylateHCID 234673511-Benzyl-2-chloromethyl-indolineHCID 24194345Phthalimide potassium saltHCID 1785127421-Benzyl-2-guanidinomethyl-indoline hemisulphate

Produkt 1

HCID 1785127432-Guanidinomethyl-indoline hemisulphate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customto give
  2. custom1 atmosphere until the reaction ceases
  3. filtrationAfter filtering
  4. customevaporating the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-fba2e1b2f2a44d9c9008b938e3f3152c
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04260628

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