Diethyl (ethoxymethylene)malonate → HCID 86614072, compound

HRID 2099125Notes

Reaction equation

HRID 2099125 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].CCCCCC.C(O[CH:19]=[C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:19]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:4][C:3]=1[CH3:9]

Participants

4

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 8058HexaneHCID 27342754-Iodo-3-methylaniline

Product 1

HCID 86614072HCID 86614072, compound

Conditions

Temperature
130 °C

Procedure

4-iodo-3-methylaniline (5.75 g) was suspended in diethyl ethoxymethylenemalonate (5.5 mL). The mixture was heated at 130° C. for 2.5 h. After cooling to ˜90° C., hexane was added and the mixture stirred while cooling to room temperature. The product crystallized out, and was filtered off, washing well with more hexane. The solid was dried in vacuo to yield the title compound as a pale grey powder (7.947 g); 1H NMR δ (CDCl3) 1.33 (3H, t), 1.38 (3H, t), 2.43 (3H, s), 4.25 (2H, q), 4.3 (2H, q), 6.69 (1H, dd), 7.01 (1H, d), 7.75 (1H, d), 8.46 (1H, d), and 10.95 (1H, br d).

Workup

  1. temperatureAfter cooling to ˜90° C.
  2. temperaturewhile cooling to room temperature
  3. customThe product crystallized out
  4. filtrationwas filtered off
  5. washwashing well with more hexane
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-32ac296b97ba4d0d84e6ff9b156cbfcb
Source dataset
uspto-grants-2009_08
Patent number
US07569550B2

Reaction notes

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