Chloroacetyl chloride → HCID 178429296, compound

HRID 1878057Notes

Reaction equation

HRID 1878057 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[CH:11]=[C:10]([CH3:15])[N:9]=2)=[N:6][CH:7]=1.C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>C1COCC1>[Cl:23][CH2:24][C:25]([NH:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[N:13]=[C:12]([OH:14])[CH:11]=[C:10]([CH3:15])[N:9]=2)=[CH:4][CH:3]=1)=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 178429295HCID 178429295, compound

Product 1

HCID 178429296HCID 178429296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound of example 13 (0.10 g, 0.49 mmol) in THF (5 mL) was added triethylamine (0.075 g, 0.742 mmol) and chloroacetylchloride (0.0559 g, 0.495 mmol), and the reaction mixture was stirred at room temperature for 2 hours. THF was removed under reduced pressure, and the reaction mixture was quenched with water and extracted with ethyl acetate (3×10 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by crystallization from ethyl acetate and petroleum ether to obtain the title compound.

Workup

  1. customTHF was removed under reduced pressure
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain the crude product, which
  7. customwas purified by crystallization from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-c98fde08bcdb46a5a95e98b638444a8e
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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