Acetyl chloride → HCID 87228678, compound

HRID 911882Notes

Reaction equation

HRID 911882 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15]/[C:16](/[NH2:19])=[N:17]/[OH:18])[N:13]=2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:33](Cl)(=[O:35])[CH3:34]>CC(C)=O>[C:33]([O:18]/[N:17]=[C:16](\[NH2:19])/[CH2:15][CH2:14][C:12]1[N:13]=[C:9]([NH:8][C:5]2[C:4]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[S:10][CH:11]=1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 87228754HCID 87228754, compound

Product 1

HCID 87228678HCID 87228678, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a suspension of (Z)-3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)-N′-hydroxypropanamidine (0.200 g, 0.460 mmol) and K2CO3 (0.070 g, 0.506 mmol) in acetone (5 mL), cooled in an ice bath, was added a solution of acetyl chloride (0.032 mL, 0.460 mmol) in 3 mL acetone and the mixture was allowed to slowly warm to ambient temperature. The reaction was concentrated to dryness, dissolved in CH2Cl2 and washed with water, dried over Na2SO4, and concentrated to give the title compound (0.205 g, 93.4% yield) that was used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. concentrationThe reaction was concentrated to dryness
  3. dissolutiondissolved in CH2Cl2
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-29553fdfe2584da88b01ae0e0f98432c
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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