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

HRID 2370239Notes

Reaction equation

HRID 2370239 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, 1.0H), 8.50 (s, 1.0H), 8.05 (d, 1.0H, J=5.4 Hz), 7.30 (d, 1.0H, 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-dda4219eefe7410090058d46cc730d39
Source dataset
uspto-grants-2014_04
Patent number
US08710075B2

Reaction notes

Loading…