Diethyl 2-((thiophen-3-ylamino)methylene)malonate → HCID 178469639, compound

HRID 1947555Notes

Reaction equation

HRID 1947555 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([NH:6][CH:7]=[C:8]([C:14]([O:16]CC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:2]1>O(C1C=CC=CC=1)C1C=CC=CC=1>[OH:16][C:14]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:6]=[C:3]2[CH:4]=[CH:5][S:1][C:2]=12

Participants

3

Reactant 1

HCID 2807580Diethyl 2-((thiophen-3-ylamino)methylene)malonate

Product 1

HCID 178469639HCID 178469639, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

The diethyl 2-((thiophen-3-ylamino)methylene)malonate 2 (1.0 g, 3.7 mmol, 1 eq) was heated to 240° C. in Ph2O (10 mL) for 6 h. After the starting material was consumed, the reaction mixture was allowed to cool to room temperature and solid was filtered. The solid was washed with water and dichloromethane to obtain the desired compound as a light brown powder (0.42 g 50% yield). LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 224.0, retention time 0.40 minutes. 1H NMR (DMSO-d6) δ: 12.80 (s, 1.0 H), 8.50 (s, 1.0 H), 8.05 (d, 1.0 H, J=5.4 Hz), 7.30 (d, 1.0 H, J=5.4 Hz), 4.20 (q, 2H, J=7.0 Hz), 4.10 (q, 2H, J=7.0 Hz), 1.30 (t, 3H, J=7.0 Hz).

Workup

  1. customAfter the starting material was consumed
  2. filtrationsolid was filtered
  3. washThe solid was washed with water and dichloromethane

Sources & evidence

ORD record
ord-1861af0083b6462697bceaab759f271e
Source dataset
uspto-grants-2013_03
Patent number
US08399479B2

Reaction notes

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