Sodium Chloride → HCID 54711424, compound

HRID 1374765Notes

Reaction equation

HRID 1374765 reaction equation
IC1C=C(N[C:10](=[O:23])[CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([I:22])[CH:16]=2)=[O:13])C=CC=1C.[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[Na+]>O>[OH:23][C:10]1[C:20]2[C:15](=[CH:16][C:17]([I:22])=[C:18]([CH3:21])[CH:19]=2)[NH:14][C:12](=[O:13])[CH:11]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 22054484HCID 22054484, compound

Product 1

HCID 54711424HCID 54711424, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
250 °C

Procedure

N,N′-Bis-(3-iodo-4-methyl-phenyl)-malonamide (43.4 g, 81.3 mmol) was added portionwise to a melt of aluminum chloride (32.5 g, 244 mmol) and sodium chloride (9.50 g, 163 mmol) at 150° C., then the mixture was heated at 250° C. for 20 min. After cooling the solid formed was suspended in hot water and collected by filtration. This crude material was suspended in hot 0.5 M aq. sodium hydroxide solution, insoluble material was removed by filtration, and the filtrate was acidified with 25% aq. hydrochloric acid solution. The precipitate was collected by filtration, washed with water and ethyl acetate, and dried to afford the title compound (6.85 g, 28%). Light brown solid, EI-MS: m/e=301.2 (M+).

Workup

  1. temperatureAfter cooling the solid
  2. customformed
  3. filtrationcollected by filtration
  4. customwas removed by filtration
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water and ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-6909e571b0a14f01be25ff232ba09f52
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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