Diethyl Ether → HCID 54326665, compound

HRID 1729079Notes

Reaction equation

HRID 1729079 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])[CH3:3].[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22](Cl)=[O:23])=[CH:18][CH:17]=1)=[O:15].CCOCC>N1C=CC=CC=1C([O-])=O>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([NH:8][C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:21][CH:20]=2)=[O:23])[CH:9]=[CH:10][CH:11]=1)[CH3:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 992943-amino-N,N-dimethylbenzylamine

Product 1

HCID 54326665HCID 54326665, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6920223PicolinateSolvent

Procedure

Equimolar amounts of 3 -(N,N-dimethylaminomethyl)aniline (XVI; R=H) (Stedman, E. J. Chem. Soc. 1927, 1902) and 4-(methoxycarbonyl) benzenecarbonyl chloride (XvII; Z=H) were reacted together in pyridineat 0 ° C., to give methyl 4-[3 -(N,N-dimethylaminomethyl)phenyl]carbamoylbenzene-carboxylate (IX; R=Z=H) (73%), mp (dilsopropyl ether) 108°-109 ° C. 1H NMR (CD3SOCD3) 10.42 (s, 1 H, CONH), 8.13 (s, 4 H, H-2',H-3'), 7.75 (s, 1H, H-2), 7.70 (d, J=8.2 Hz, 1 H, H-6), 7.30 (t, J=8.2 Hz, 1 H, H-3), 7.04 (d, J=8.2 Hz, 1 H, H-4), 3.97 (s, 3H, COOCH3), 3.40 (s, 2 H, CH2), 2.18 (s , 6 H, N (CH3)2).Anal.(C18H 20 N2O3) C, H, N.

Sources & evidence

ORD record
ord-8e3e13ebc9b6446db52a9780a97066d8
Source dataset
uspto-grants-1994_07
Patent number
US05331004

Reaction notes

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