Diethyl (ethoxymethylene)malonate → Diethyl 2-{[4-(hydroxymethyl)-2-iodoanilino]methylene}malonate

HRID 2086605Notes

Reaction equation

HRID 2086605 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[I:10].C(O[CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])C>C(Cl)Cl.CO>[OH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:3]([I:10])[CH:4]=1

Participants

5

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 22724559(4-Amino-3-iodophenyl)methanol

Product 1

HCID 22724545Diethyl 2-{[4-(hydroxymethyl)-2-iodoanilino]methylene}malonate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (4-amino-3-iodophenyl)methanol (5.97 g) and diethyl ethoxymethylenemalonate (5.34 mL) is heated at 100° C. for 30 min. The reaction is cooled to room temperature. The resulting solid is dissolved in a mixture of CH2Cl2 and MeOH, adsorbed onto silica and chromatographed (Biotage flash 40M, eluent CH2Cl2 (1L), 0.5% MeOH/CH2Cl2 (5L)). Product containing fractions are combined and condensed to afford diethyl 2-{[4-(hydroxymethyl)-2-iodoanilino]methylene}malonate as a white solid.

Workup

  1. customchromatographed (Biotage flash 40M, eluent CH2Cl2 (1L), 0.5% MeOH/CH2Cl2 (5L))
  2. additionProduct containing fractions
  3. customcondensed

Sources & evidence

ORD record
ord-881d38ee7edb4068960ffb869cfabdde
Source dataset
uspto-grants-2004_04
Patent number
US06727248B2

Reaction notes

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