Acetic Anhydride → 2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

HRID 1885370Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:17](O)=O)[N:9]([C:11](=O)[C:12]([F:15])([F:14])[F:13])[CH3:10])=[CH:4][CH:3]=1.ClC(=C)[C:22]#[N:23].[C:25](OC(=O)C)(=O)C.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:10])[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:25][C:17]=2[C:22]#[N:23])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-(p-chlorophenyl)-N-(trifluoroacetyl)sarcosine (147.7 g, 0.50 mol) in acetonitrile is treated dropwise with α-chloroacrylonitrile (54.7 g, 0.62 mol) and acetic anhydride (153 g, 1.5 mol), stirred vigorously, treated dropwise with triethylamine (58.1 g, 0.57 mol) at 56°-60° C. over a 11/4 hour period, heated at 60° C. for 16 hours and concentrated in vacuo to give a residue. The residue is partitioned between ethyl acetate and water. The organic phase is concentrated in vacuo to afford an amber solid residue. Said solid is purified by flash chromatography (silica; ethyl acetate/hexanes) and recrystallized from methanol to give the title product as a pale yellow solid, mp 129.5°-130.5° C.

Workup

concentrationconcentrated in vacuo
customto give a residue
customThe residue is partitioned between ethyl acetate and water
concentrationThe organic phase is concentrated in vacuo
customto afford an amber solid residue
customis purified by flash chromatography (silica; ethyl acetate/hexanes)
customrecrystallized from methanol

Sources & evidence

ORD record: ord-97ed2fd1de4546a3b2b70d1f4686699d
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05144041

Reaction notes

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