Chloroacetyl chloride → HCID 86724240, compound

HRID 873701Notes

Reaction equation

HRID 873701 reaction equation
[NH2:1][C:2]1([CH2:16][OH:17])[C:11]2([CH2:14][O:13][CH2:12]2)[CH2:10][O:9][C:8]2[C:3]1=[CH:4][C:5]([Br:15])=[CH:6][CH:7]=2.C([O-])(O)=O.[Na+].[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl>[Br:15][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][CH:6]=1)[O:9][CH2:10][C:11]1([CH2:14][O:13][CH2:12]1)[C:2]2([NH:1][C:25](=[O:26])[CH2:24][Cl:23])[CH2:16][OH:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 516892Sodium BicarbonateHCID 86724241HCID 86724241, compound

Product 1

HCID 86724240HCID 86724240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of (4-amino-6-bromo-4H-spiro[chromene-3,3′-oxetan]-4-yl)methanol (280 mg, 0.933 mmol), CH2Cl2 (10 mL) and saturated aqueous NaHCO3 (10 mL) was added a mixture of chloroacetyl chloride (0.083 mL, 1.02 mmol) and CH2Cl2 (1 mL) at ambient temperature. After stirring for 30 minutes at ambient temperature, chloroacetyl chloride (0.016 mL, 0.197 mmol) was added to the reaction mixture. The mixture was stirred for 10 minutes at ambient temperature, diluted with CH2Cl2 and separated. The organic layer was washed with water, dried over MgSO4 and filtered. Concentration of the filtrate at reduced pressure gave crude N-[6-bromo-4-(hydroxymethyl)-4H-spiro[chromene-3,3′-oxetan]-4-yl]-2-chloroacetamide, which was used for the next reaction without further purification.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 10 minutes at ambient temperature
  3. customseparated
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-3722d921743b4dd1876ac1351a8ac67a
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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