Sodium Iodide → HCID 67926077, compound

HRID 1382958Notes

Reaction equation

HRID 1382958 reaction equation
Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:8])=[C:5]([OH:20])[CH:4]=1.[C:21](=[O:24])([O-])[O-:22].[K+].[K+].[I-].[Na+].Cl[CH2:30][C:31]([NH2:33])=[O:32]>>[OH2:8].[C:21]([OH:22])(=[O:24])[CH3:3].[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])=[O:8])=[C:5]([O:20][CH2:30][C:31]([NH2:33])=[O:32])[CH:4]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 67926077HCID 67926077, compoundYield 79.7%

Procedure

A well stirred mixture of 4-amino-5-chloro-N-[2(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (2.0 g, 6.2 mmoles), potassium carbonate (2.57 g, 18.6 mmoles), sodium iodide (0.93 g, 6.8 mmoles) and 2-chloroacetamide (0.64 g, 6.8 mmoles) was heated at 75° for 3 hours. The mixture was then evaporated in vacuo and the residue partitioned between water and methylene chloride. The aqueous phase was extracted twice with methylene chloride, and the combined extracts treated with an excess of acetic acid followed by concentration in vacuo. The semi-solid residue was treated with methylene chloride (150 ml) and filtered to give a colorless solid. This was recrystallized from acetonitrile to give 1.04 g (41%) of the title compound as an off-white solid, mp 116°-125°. The NMR spectrum (90 MHz) in D2O gave the following resonances: δ7.8 (s, 1H); 6.26 (1H, s); 4.8 (s, 2H); 3.8 (m, 2H); 3.3 (m, 6H); 1.95 (s, 3H); 1.3 (t, 6H).

Workup

  1. temperaturewas heated at 75° for 3 hours
  2. customThe mixture was then evaporated in vacuo
  3. customthe residue partitioned between water and methylene chloride
  4. extractionThe aqueous phase was extracted twice with methylene chloride
  5. additionthe combined extracts treated with an excess of acetic acid
  6. concentrationfollowed by concentration in vacuo
  7. additionThe semi-solid residue was treated with methylene chloride (150 ml)
  8. filtrationfiltered
  9. customto give a colorless solid
  10. customThis was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b8c8764eee434a2688f4b74aec908262
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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