Water → Diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate

HRID 1060595Notes

Reaction equation

HRID 1060595 reaction equation
[OH:1][CH2:2][C:3]1[CH:21]=[CH:20][C:6]([NH:7][CH:8]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([I:22])[CH:4]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].O>C(O)(=O)C>[C:23]([O:1][CH2:2][C:3]1[CH:21]=[CH:20][C:6]([NH:7][CH:8]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([I:22])[CH:4]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 22724545Diethyl 2-{[4-(hydroxymethyl)-2-iodoanilino]methylene}malonate

Product 1

HCID 22724556Diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonateYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of diethyl 2-{[4-(hydroxymethyl)-2-iodoanilino]methylene}malonate (0.20 g) and acetic anhydride (0.054 mL) in acetic acid (0.24 mL) is heated at 80° C. overnight. The reaction is cooled to room temperature and poured into 50 mL of water. The resulting solid is filtered and dried to yield 0.19 g (87%) of diethyl 2-({4-[(acetyloxy)methyl]-2-iodoanilino}methylene)malonate as a white solid, m.p. 128-131° C.

Workup

  1. filtrationThe resulting solid is filtered
  2. customdried

Sources & evidence

ORD record
ord-ceb6a0373fd44fec91417ccc7704f62c
Source dataset
uspto-grants-2003_02
Patent number
US06525049B2

Reaction notes

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