Diethyl Malonate → HCID 69607336, compound

HRID 1244089Notes

Reaction equation

HRID 1244089 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH2:18])=[O:5])[CH3:2].[C:19](OCC)(=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[CH2:1]([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 7761Diethyl MalonateHCID 616598Ethyl 2-amino-4-(4-chlorophenyl)thiophene-3-carboxylate

Product 1

HCID 69607336HCID 69607336, compound

Procedure

A solution of 2-Amino-4-(4-chloro-phenyl)-thiophene-3-carboxylic acid ethyl ester (4a) (1.759 g, 6.24 mmol) in diethyl malonate (8.0 g, 50 mmol) was heated at 180° C. for 4 hours. The excess diethyl malonate was removed under reduced pressure to give the title compound. MS (DCI/NH3) m/e 396 (M+H)+; 1H NMR (300 MHz, CDCl3): δ ppm 12.21 (s, 1H), 7.33–7.20 (m, 5H), 6.62 (s, 1H), 4.31 (q, J=7.12, 2H), 4.15 (q, J=7.12, 2H), 3.61 (s, 2H), 1.33 (t, J=7.12, 3H), 0.99 (t, J=7.12, 3H).

Workup

  1. customThe excess diethyl malonate was removed under reduced pressure

Sources & evidence

ORD record
ord-cf192db03847445880e9de4a16861e24
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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