3-Sulfolene → N,N'-bis(1,1-dioxotetrahydro-3-thienyl)-1,2-diaminopropane

HRID 268041

Reaction equation

[S:1]1(=[O:7])(=[O:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.[NH2:8][CH2:9][CH:10]([NH2:12])[CH3:11].[OH-:13].[Na+]>C(O)C>[O:6]=[S:1]1(=[O:7])[CH2:5][CH2:4][CH:3]([NH:8][CH2:9][CH:10]([NH:12][CH:3]2[CH2:4][CH2:5][S:1](=[O:6])(=[O:13])[CH2:2]2)[CH3:11])[CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a 500 ml round-bottom flask equipped with condenser, thermometer and a stirrer were introduced 118 g. (1.0 mole) of 2,5-dihydrothiophene 1,1-dioxide, 200 ml. of 70% by weight aqueous ethanol and 37 g (0.5 mole) of 1,2-diaminopropane and 10 ml. of a 0.1 N sodium hydroxide solution. The reaction mixture was heated at 85°C for 20 hours. The solvent was then removed under a reduced pressure. The product, N,N'-bis(1,1-dioxotetrahydro-3-thienyl)-1,2-diaminopropane was obtained as a viscous liquid. The infrared spectrum of this product was superimposable with that of Example 3. This product also evaluated in high resiliency, flexible polyurethane foam (see Example 19).

Workup

customTo a 500 ml round-bottom flask equipped with condenser
additionthermometer and a stirrer were introduced 118 g
customThe solvent was then removed under a reduced pressure

Sources & evidence

ORD record: ord-ee58488f61d34303b068a65c1769dc69
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03946038

Linked notes

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