Chlorosuccinimide → 2-chloro-2-methylthio-N-(2-methylpent-3-yn-2-yl)acetamide

HRID 563888Notes

Reaction equation

[CH3:1][S:2][CH2:3][C:4]([NH:6][C:7]([CH3:12])([C:9]#[C:10][CH3:11])[CH3:8])=[O:5].[Cl:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:13][CH:3]([S:2][CH3:1])[C:4]([NH:6][C:7]([CH3:12])([C:9]#[C:10][CH3:11])[CH3:8])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

The product of Step 1 (0.824 g) was dissolved in carbon tetrachloride (15 ml) with warming. The solution was then cooled to 0° C. and N-chlorosuccinimide (NCS, 0.653 g) was then gradually added and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was filtered to remove succinimide and the resulting liquid was evaporated to give 2-(chloro)-2-(methylthio)-N-(2-methylpent-3-yn-2-yl) acetamide as a clear oil (1.4 g), which was used without further purification.

Workup

temperaturewith warming
filtrationThe reaction mixture was filtered
customto remove succinimide
customthe resulting liquid was evaporated

Sources & evidence

ORD record: ord-3e105cff6cdb43a3a46d8d5a2a7bebfa
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067592B2

Reaction notes

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