Acetyl chloride → HCID 22093064, compound

HRID 1182209Notes

Reaction equation

HRID 1182209 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[S:14][N:13]=[N:12][C:11]=2[C:15]([NH2:17])=[O:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:18](Cl)(=[O:20])[CH3:19]>CN(C=O)C>[C:18]([NH:17][C:15]([C:11]1[N:12]=[N:13][S:14][C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:16])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 5148325HCID 5148325, compound

Product 1

HCID 22093064HCID 22093064, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cooled suspension of NaH (16 mg 60% in oil, 0.23 mmole) in 1.5 mL of DMF was added 0.5 mL of DMF solution of 5-phenylamino-[1,2,3]thiadiazole-4-carboxylic acid amide (50 mg, 0.23 mmole). The mixture was stirred at room temperature for 1 h, and then cooled in an ice bath. To the cooled solution was added acetyl chloride (18.6 mg, 0.24 mmole), resulting in the formation of a yellowish solution that was kept stirring at room temperature for 1.5 h. The reaction was then quenched with a mixture of 5 mL of saturated aqueous NH4Cl, 5 mL of saturated aqueous NaCl and 5 mL of EtOAc. The aqueous phase was extracted with EtOAc (2×6 mL). The combined organic layers were dried with Na2SO4, concentrated, and then loaded onto a preparative TLC plate, which was sequentially eluted with hexane-EtOAc (2:1) and EtOAc-acetone-H2O (4:1:0.15). The product (24 mg) was obtained as a yellowish solid. 1H NMR (ppm, in DMSO-d6): 12.84 (s, br., 1H), 7.79 (d, 2H), 7.64 (s, br., 1H), 7.53 (t, 2H), 7.40 (t, 1H), 2.39 (s, 3H).

Workup

  1. temperaturecooled in an ice bath
  2. customresulting in the formation of a yellowish solution that
  3. stirringwas kept stirring at room temperature for 1.5 h
  4. customThe reaction was then quenched with a mixture of 5 mL of saturated aqueous NH4Cl, 5 mL of saturated aqueous NaCl and 5 mL of EtOAc
  5. extractionThe aqueous phase was extracted with EtOAc (2×6 mL)
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. concentrationconcentrated
  8. washwas sequentially eluted with hexane-EtOAc (2:1) and EtOAc-acetone-H2O (4:1:0.15)

Sources & evidence

ORD record
ord-2c249991dc3d40f79cf3e4b3f4f44525
Source dataset
uspto-grants-2007_10
Patent number
US07288556B2

Reaction notes

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