Thionyl Chloride → N-(2-Cyanoethyl)-4'-methylbiphenyl-2-carboxyamide

HRID 653948Notes

Reaction equation

HRID 653948 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14](O)=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C(O)(=O)/C=C/[C:24](O)=[O:25].[NH2:29][CH2:30][CH2:31][C:32]#[N:33]>>[C:32]([CH2:31][CH2:30][NH:29][C:24]([CH2:14][C:9]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:25])#[N:33]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 815682-(4-Methylphenyl)benzoic acidHCID 6433176Propanenitrile, 3-amino-, (2E)-2-butenedioate (1:1)

Product 1

HCID 131717460N-(2-Cyanoethyl)-4'-methylbiphenyl-2-carboxyamideYield 80,085.5%

Procedure

4'-Methylbiphenyl-2-carboxylic acid (50.0 g, 0.24 mmol) was converted into the corresponding acid chloride as described in Example 89, Part B using thionyl chloride. This acid chloride was subsequently reacted with 3-aminopropionitrile fumarate (30.25 g, 0.24 mmol) under Schotten-Baumann reaction conditions described in Example 209, Part B to yield 53.50 g of white powder after recrystallization from methylcylcohexane/butylchloride; m.p. 102.0-103.5° C. NMR (200 MHz, CDCl3): δ 7.68 (d, 1H, J=7Hz); 7.56-7.19 (m, 7H); 5.65 (bm, 1H); 3.43 (d of t, 2H, J=7,7Hz); 2.39 (t, 2H, J=7Hz). Anal. calcd. for C17H16N2O: C, 77.25; H, 6.10; N, 10.60. Found: C, 77.42; H, 6.40; N, 10.68.

Sources & evidence

ORD record
ord-c993a56183ac4e13adf8d5f2301d59cb
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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