2-(Methylamino)ethanol → 2-(Methyl(2-hydroxyethyl)amino)benzothiazole

HRID 257169

Reaction equation

Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][NH:12][CH2:13][CH2:14][OH:15]>O>[CH3:11][N:12]([CH2:13][CH2:14][OH:15])[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-chlorobenzothiazole (8.5 g) and 2-methylaminoethanol (20 ml) was heated at 120° C. under pressure in a sealed, glass lined, stainless steel reaction vessel for 18 hours. After cooling, the oil was added to water (100 ml), extracted with dichloromethane (2×100 ml), the organic extracts were dried (MgSO4), filtered and evaporated to dryness. Chromatography of the residual oil on silica-gel in 21/2% methanol in dichloromethane gave the title compound which was used in Preparation 1 without further purification.

Workup

temperatureAfter cooling
extractionextracted with dichloromethane (2×100 ml)
dry with materialthe organic extracts were dried (MgSO4)
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-6d84f11f982a47ae8240ea0f0041acd5
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05260445

Linked notes

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