Ethyl cyanoacetate → HCID 86584820, compound

HRID 1835305Notes

Reaction equation

[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](Cl)=[N:11][CH:10]=1.[C:34]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])#[N:35].CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O>[CH2:40]([O:39][C:37](=[O:38])[CH:36]([C:12]1[CH:13]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:9]([C:8](=[O:23])[N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:32])([F:33])[F:1])[CH:27]=[C:26]([C:28]([F:30])([F:31])[F:29])[CH:25]=2)[CH3:24])=[CH:10][N:11]=1)[C:34]#[N:35])[CH3:41]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1.00 g (2.05 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-chloro-N-methyl-4-o-tolyl-nicotinamide, 0.44 ml (4.1 mmol) ethyl cyanoacetate and 0.46 g (4.1 mmol) potassium tert-butoxide in 2 ml dimethyl sulfoxide was stirred at 100° C. over night. After cooling to room temperature 10 ml of a half-concentrated aqueous solution of ammonium chloride was added. The mixture was extracted with 3 portions of ethyl acetate. The combined organic extracts were washed with two portions of water, dried with sodium sulfate and concentrated to give 1.2 g of crude product. Flash chromatography afforded 0.681 g (58.8%) of the title compound as a yellow foam.

Workup

additionwas added
extractionThe mixture was extracted with 3 portions of ethyl acetate
washThe combined organic extracts were washed with two portions of water
dry with materialdried with sodium sulfate
concentrationconcentrated
customto give 1.2 g of crude product

Sources & evidence

ORD record: ord-2f270c0414f643a4b4c5d1ed17b59d97
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770637B2

Reaction notes

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