Chloroacetyl chloride → HCID 22982929, compound

HRID 1862504Notes

Reaction equation

HRID 1862504 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].[F:10][C:11]([F:25])([F:24])[C:12]([NH:14][C@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1)=[O:13]>ClCCCl>[Cl:5][CH2:6][C:7]([C:21]1[CH:22]=[C:23]2[C:18]([CH2:17][CH2:16][C@H:15]2[NH:14][C:12](=[O:13])[C:11]([F:24])([F:10])[F:25])=[CH:19][CH:20]=1)=[O:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14511478HCID 14511478, compound

Product 1

HCID 22982929HCID 22982929, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

To a suspension of AlCl3 (89.2 g, 0.67 mol) in 1,2-dichloroethane (600 ml) was added chloroacetyl chloride (55.7 ml, 78.9 g, 0.7 mol) dropwise at 0-5° C. under nitrogen for 20 minutes and it was then left to warm up to 20-25° C. To this mixture was added N-trifluoroacetyl-(R)-1-aminoindan (34.4 g, 0.15 mol) for 3 hours at 20-25° C. The resulting mixture was then stirred for an additional 30 minutes and poured into a mixture of ice-cold water (1.5 l) and 1,2-dichloroethane (1l). The mixture was stirred for 5 minutes and the layers were separated. The aqueous layer was extracted with 1,2-dichloroethane (2×750 ml). The combined organic layers were washed with water (2×900 ml) and 5% aqueous NaHCO3 solution (3×900 ml). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give a solid, which was recrystallized from ethanol to give 15 g (48%) of a white solid mp: 166-167° C.

Workup

  1. waitit was then left
  2. stirringThe mixture was stirred for 5 minutes
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with 1,2-dichloroethane (2×750 ml)
  5. washThe combined organic layers were washed with water (2×900 ml) and 5% aqueous NaHCO3 solution (3×900 ml)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customthe solvent was removed under reduced pressure
  8. customto give a solid, which
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-fd1496b933e84abd9eecaba175fc67d1
Source dataset
uspto-grants-2003_03
Patent number
US06538025B2

Reaction notes

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