Allyl isocyanate → 4-(Allylcarbamoyloximino)-5-methyl-1,3-oxathiolane

HRID 1076403Notes

Reaction equation

HRID 1076403 reaction equation
[CH2:1]([N:4]=[C:5]=[O:6])[CH:2]=[CH2:3].[N:7](=[C:9]1[CH:13]([CH3:14])[O:12][CH2:11][S:10]1)[OH:8]>CCOCC.C(N(CC)CC)C>[CH2:1]([NH:4][C:5]([O:8][N:7]=[C:9]1[CH:13]([CH3:14])[O:12][CH2:11][S:10]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 15123Allyl isocyanateHCID 71364792N-(5-Methyl-1,3-oxathiolan-4-ylidene)hydroxylamine

Product 1

HCID 1713364-(Allylcarbamoyloximino)-5-methyl-1,3-oxathiolane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 8471TriethylamineSolvent

Procedure

A quantity of 3 ml of allyl isocyanate was caused to react with 3 grams of 4-oximino-5-methyl-1,3-oxathiolane dissolved in 50 ml of ether containing 2 drops of triethylamine over a period of 20 hours at room temperature. Conventional workup and recrystallization from isopropyl ether afforded 3 grams of product, mp 66.0°-67.5°, structure confirmed by spectral analysis.

Workup

  1. customConventional workup and recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-b70d4e6f4369405491150e82c996e66a
Source dataset
uspto-grants-1976_05
Patent number
US03956500

Reaction notes

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