Chloroacetone → HCID 49871062, compound

HRID 1951355Notes

Reaction equation

HRID 1951355 reaction equation
[NH2:1][C:2]1[C:7]([I:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1.Cl[CH2:11][C:12](=O)[CH3:13]>C(O)C>[NH2:9][C:6]1[CH:5]=[CH:4][N:3]2[CH:11]=[C:12]([CH3:13])[N:1]=[C:2]2[C:7]=1[I:8]

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 67361467HCID 67361467, compound

Product 1

HCID 49871062HCID 49871062, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2,4-diamino-3-iodopyridine 22 (4.36 g, 18.6 mmol) in ethanol (100 mL) was added chloracetone (7.15 g, 77.3 mmol). The solution was stirred at 65° C. for 6 h. After cooling to room temperature, the solution was evaporated to dryness. The residue was diluted with water (75 mL) and the resulting solution made basic (pH=12-13) by the addition of a ammonium hydroxide solution. The solution was extracted with CH2Cl2 and the combinated extracts were dried (Na2SO4), filtered and evaporated under reduced pressure. The crude product was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford compound 23 (3.30 g, yield: 65%); mp 185° C.; IR (KBr) 3454, 3431, 3355, 3093, 3026, 1646, 1499, 1463; 1H NMR (400 MHz, DMSO-d6) δ 2.19 (s, 3H), 5.68 (brs, 2H), 6.38 (d, 1H, J=7.1 Hz), 7.42 (s, 1H), 8.03 (d, 1H, J=7.1 Hz); 13C NMR (100 MHz, DMSO-d6) δ 14.1, 60.9, 103.8, 109.3, 126.0, 140.4, 145.6, 146.6. Anal. Calcd for C8H8IN3: C, 35.19; H, 2.95; N, 15.39. Found: C, 35.25; H, 2.92; N, 15.60.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solution was evaporated to dryness
  3. additionThe residue was diluted with water (75 mL)
  4. additionby the addition of a ammonium hydroxide solution
  5. extractionThe solution was extracted with CH2Cl2
  6. dry with materialthe combinated extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-0b736827973e4415b7d2b82506bca560
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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