HCID 21947422, compound → HCID 73738617, compound

HRID 2214732Notes

Reaction equation

HRID 2214732 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8](Cl)=[O:9])[C:4](=[O:11])[O:3]1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:17][NH:18][O:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[Cl:13][C:14]1[CH:15]=[C:16]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:17][N:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1)[C:8](=[O:9])[CH:7]=[C:5]1[C:4](=[O:11])[O:3][C:2]([CH3:12])([CH3:1])[O:6]1

Participants

3

Reactant 2

HCID 21947422HCID 21947422, compoundHCID 85435482(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride

Product 1

HCID 73738617HCID 73738617, compoundYield 65%

Procedure

Reaction of (2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetyl chloride (0.49 mmol) with N-(3,4-dichlorobenzyl)-O-(3-morpholin-4-yl-propyl)-hydroxylamine (0.150 g, 0.49 mmol) as described in the preparation of compound 44-C gave 0.150 g (65% yield) of the title amide as white crystals after chromatography on silica gel: mp 77–78° C. (ether-hexane). 1HNMR 400 MHz (C6D6) δ (ppm): 1.09 (6H, s, CH3), 1.47 (2H, m, CH2), 2.17 (2H, t, J=6.5 Hz, NCH2), 2.22 (4H, m, NCH2), 3.66 (2H, t, J=6.0 Hz, OCH2), 3.73 (4H, m, OCH2), 4.56 (2H, s, NCH2), 6.82 (1H, s, CH), 6.98 (1H, dd, J=2.0 Hz and J=8.0 Hz, aromatic), 7.06 (1H, d, J=8.0 Hz, aromatic), 7.40 (1H, d, J=2.0 Hz, aromatic). Anal. Calcd for C21H26Cl2N2O6: C, 53.28; H, 5.53; N, 5.91. Found: C, 53.31; H, 5.67; N, 5.77.

Sources & evidence

ORD record
ord-ac35046807f0489f94323215d3acbf71
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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