N,N,N-trimethyl-1,1-bis(1-methylethoxy)amine → 2-(2,4-Dichloro-phenyl)-5-((e)-3-dimethylamino-acryloyl)-1h-pyrrole-3-carbonitrile

HRID 1948836Notes

Reaction equation

[C:1]([C:4]1[NH:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])=[C:6]([C:17]#[N:18])[CH:5]=1)(=[O:3])[CH3:2].C(O[CH:23](OC(C)C)[N:24]([CH3:26])[CH3:25])(C)C>C1(C)C=CC=CC=1>[Cl:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[C:7]1[NH:8][C:4]([C:1](=[O:3])/[CH:2]=[CH:23]/[N:24]([CH3:26])[CH3:25])=[CH:5][C:6]=1[C:17]#[N:18]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 5-acetyl-2-(2,4-dichloro-phenyl)-1H-pyrrole-3-carbonitrile (6.2 g, 22.21 mmol) in 155 mL of toluene was added N,N-dimethylformamide diisopropyl acetal (18.6 mL; 88.85 mmol). The mixture was allowed to stir for 34 hours at 70° C. Then, a further amount of reagent was added (4.6 mL; 22.21 mmol) and the mixture was heated to 80° C. for additional 18 hours under efficient stirring.

Workup

additionThen, a further amount of reagent was added (4.6 mL; 22.21 mmol)
temperaturethe mixture was heated to 80° C. for additional 18 hours under efficient stirring

Sources & evidence

ORD record: ord-88114d4f9ab542728816e6acbae3e699
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399668B2

Reaction notes

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