3-Methyl-2-butenoyl chloride → 3-Methylbut-2-enoyl isothiocyanate

HRID 1054921Notes

Reaction equation

[S-:1][C:2]#[N:3].[K+].[CH3:5][C:6]([CH3:11])=[CH:7][C:8](Cl)=[O:9]>ClCCl.COCCOCCOCCOCCOCCOCCO>[CH3:5][C:6]([CH3:11])=[CH:7][C:8]([N:3]=[C:2]=[S:1])=[O:9]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of potassium thiocyanate (10 g, 101 mmol, Eq: 1.00) and hexaethylene glycol monomethyl ether (896 mg, 830 μl, 3.02 mmol, Eq: 0.03) in dry dichloromethane (120 ml) was added dropwise at 0° C. a solution of 3-methylbut-2-enoyl chloride (12.0 g, 11.2 ml, 101 mmol, Eq: 1.00) in dry dichloromethane (20.0 ml) over 1 hour under argon atmosphere. After the addition was completed, the mixture (now light brown & turbid) was allowed to warm to 25° C. and was stirred for additional 3 hours. The mixture was filtrated, the filtrate was evaporated the residue was distilled under reduced pressure affording 3-methyl-but-2-enoyl isothiocyanate (9.989 g/70.2%) as a yellow liquid. GC-MS: m/ei=141 (M)/bp: 86° C./2 mbar

Workup

additionAfter the addition
filtrationThe mixture was filtrated
customthe filtrate was evaporated the residue
distillationwas distilled under reduced pressure

Sources & evidence

ORD record: ord-f8e3dfd69493417eb1f8b35517192db0
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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