Allylamine → 925-02-0

HRID 1154518Notes

Reaction equation

HRID 1154518 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[C:5]1(=[O:11])[O:10][C:8](=[O:9])[CH:7]=[CH:6]1>C1COCC1>[CH2:1]([NH:4][C:5](=[O:11])/[CH:6]=[CH:7]\[C:8]([OH:10])=[O:9])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 7923Maleic Anhydride

Product 1

HCID 1551409925-02-0

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Allylamine reacts readily with maleic anhydride in THF to give N-allylmaleamic acid (VIII) in quantitative yield. VIII reacts with bisulfite in water to form 3-carboxy-3-sulfo-N-allyl propionamide (IX). At 160° C., (IX) cyclolyzes slowly to form N-allyl-sulfo-succinimide (X).

Sources & evidence

ORD record
ord-950044d5d04f49959f91676d35a2040d
Source dataset
uspto-grants-1984_12
Patent number
US04490308

Reaction notes

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