N-(4-Fluorophenyl)-4-methylbenzylamine → 2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-phenyl)-N-(4-methyl-benzyl)-acetamide

HRID 392836Notes

Reaction equation

HRID 392836 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:28])[O:22][C:21](=[O:23])/[C:20](=[CH:24]/[C:25](Cl)=[O:26])/[O:19]1>>[CH3:17][C:18]1([CH3:28])[O:19][C:20](=[CH:24][C:25]([N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)=[O:26])[C:21](=[O:23])[O:22]1

Participants

3

Reactant 2

HCID 292877N-(4-Fluorophenyl)-4-methylbenzylamineHCID 12147055(Z)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)acetyl chloride

Product 1

HCID 697715032-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-phenyl)-N-(4-methyl-benzyl)-acetamide

Procedure

Acylation of (4-fluorophenyl)-(4-methylbenzyl)-amine (Pombrik, S. I. et al., Izv. Akad. Nauk. SSSR Ser. Khim., 10, 1981, 2406-2408) with (Z)-2,2-dimethyl-5-(chlorocarbonylmethylene)-1,3-dioxolan-4-one as described in the preparation of Intermediate 71A gave the title amide as a syrup. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.72 (6H, s, CH3), 2.31 (3H, s, CH3) 4.87 (2H, s, NCH2), 5.63 (1H, s, CH), 6.93-7.11 (8H, m, aromatics). HRMS (MAB N2) calculated for C21H20FNO4 [M−]: 369.137637: found: 369.137900.

Sources & evidence

ORD record
ord-f13c6e8b7dc441729c048dc9b5886270
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Reaction notes

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