Isopropyl 4-cyano-5-ethylthiophene-2-carboxylate → Isopropyl 5-ethyl-4-(aminothioxomethyl)-5-ethylthiophene-2-carboxylate

HRID 1058468Notes

Reaction equation

HRID 1058468 reaction equation
[NH2:1][C:2](=[S:16])[C:3]1[CH:4]=[C:5]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[S:6][C:7]=1[CH2:8][CH3:9].[C:17]([C:19]1C=C(C(OC(C)C)=O)SC=1CC)#N>>[CH2:8]([C:7]1([CH2:17][CH3:19])[S:6][CH:5]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[CH:4]=[C:3]1[C:2]([NH2:1])=[S:16])[CH3:9]

Participants

3

Reactant 2

HCID 18537065Isopropyl 4-cyano-5-ethylthiophene-2-carboxylateHCID 18672186Isopropyl 4-(aminothioxomethyl)-5-ethylthiophene-2-carboxylate

Product 1

HCID 18536974Isopropyl 5-ethyl-4-(aminothioxomethyl)-5-ethylthiophene-2-carboxylateYield 74%

Procedure

Isopropyl 4-(aminothioxomethyl)-5-ethylthiophene-2-carboxylate: A stirred solution of 1.7 g (7.6 mmol) of isopropyl 4-cyano-5-ethylthiophene-2-carboxylate was treated as in Example 139, step (c) to give isopropyl 5-ethyl-4-(aminothioxomethyl)-5-ethylthiophene-2-carboxylate (1.45 g, 74%) as a yellow solid. 1H-NMR (DMSO-d6; 300 MHz) δ 9.93 (br s, 1H), 9.39 (br s, 1H), 8.04 (s, 1H), 5.08 (septet, 1H, J=6.2 Hz), 3.08 (q, 2H, J=7.5 Hz), 1.29 (d, 6H, J=6.2 Hz), 1.24 (t, 3H, J=7.5 Hz).

Sources & evidence

ORD record
ord-3f0b8775552b4a51b70c87804f1d889b
Source dataset
uspto-grants-2003_02
Patent number
US06515002B2

Reaction notes

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