Acetyl chloride → HCID 59565732, compound

HRID 2075948Notes

Reaction equation

HRID 2075948 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][C:12]([I:19])=[C:13]([CH:18]=1)[C:14]([NH:16][OH:17])=[NH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](Cl)(=O)[CH3:23]>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][C:12]([I:19])=[C:13]([C:14]2[N:15]=[C:22]([CH3:23])[O:17][N:16]=2)[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178492958HCID 178492958, compound

Product 1

HCID 59565732HCID 59565732, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 5-benzyloxy-N-hydroxy-2-iodo-4-methoxy-benzamidine (reference example 3-3) (20 g) and pyridine (115 mL) was added acetyl chloride (3.8 mL) under ice-bath cooling. After stirring at the same temperature for 3 hours, the mixture was stirred and heated at 120° C. for 3 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and 2 mol/L hydrochloric acid. The separated organic layer was washed with 2 mol/L hydrochloric acid and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 15%-50% ethyl acetate/hexane, gradient elution) to give the title compound (17.0 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred
  3. temperatureAfter cooling to room temperature
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionTo the residue were added ethyl acetate and 2 mol/L hydrochloric acid
  6. washThe separated organic layer was washed with 2 mol/L hydrochloric acid and brine successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: 15%-50% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-c6f24d2028eb40499dd3461567297ab0
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

Loading…