Acetoxyacetyl chloride → HCID 59353085, compound

HRID 1914720Notes

Reaction equation

HRID 1914720 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:21]([Cl:22])=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:23]([O:26][CH2:27][C:28](Cl)=[O:29])(=[O:25])[CH3:24].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[C:23]([O:26][CH2:27][C:28]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[C:21]([Cl:22])=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1)=[O:29])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 26297Acetoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 3302617HCID 3302617, compound

Product 1

HCID 59353085HCID 59353085, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-amino-N-(3-chloroquinoxalin-2-yl)benzenesulfonamide (2 g; 4.49 mmol; 1 eq) in DCM (100 mL) is added acetoxyacetyl chloride (1.23 mL; 9 mmol; 2 eq) and N-ethyldiisopropylamine (2.3 mL; 13.5 mmol; 3 eq) and the reaction mixture is stirred at room temperature for 30 min. DCM is removed under reduced pressure and the crude residue is dissolved in EtOAc. The organic phase is washed twice with 10% citric acid then brine. The solvent is evaporated and the residue is taken up in iPrOH then refluxed and left at room temperature until precipitation. The precipitate is filtered off then dried under reduced pressure to afford 1.9 g (95%) of the title compound as a yellow powder. 1H NMR (DMSO-d6) δ 10.70 (s, 1H), 8.25 (m, 2H), 8.09 (m, 4H), 7.88 (m, 2H), 4.71 (s, 2H), 2.13 (s, 3H). HPLC (max plot) 98%; Rt 4.03 min. UPLC/MS (ES+) 435.2.

Workup

  1. customDCM is removed under reduced pressure
  2. dissolutionthe crude residue is dissolved in EtOAc
  3. washThe organic phase is washed twice with 10% citric acid
  4. customThe solvent is evaporated
  5. temperaturethen refluxed
  6. waitleft at room temperature until precipitation
  7. filtrationThe precipitate is filtered off
  8. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-04eac3868a514b3892b927e53b360477
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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