Chloroacetyl chloride → HCID 18519875, compound

HRID 1368063Notes

Reaction equation

HRID 1368063 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([C:13]1[CH:17]=[CH:16][NH:15][CH:14]=1)=[O:12].[Cl:18][CH2:19][C:20](Cl)=[O:21].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Cl:18][CH2:19][C:20]([C:16]1[NH:15][CH:14]=[C:13]([C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[O:12])[CH:17]=1)=[O:21]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 10489167HCID 10489167, compound

Product 1

HCID 18519875HCID 18519875, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 12.82 g (0.058 mole) of 3-(2-naphthalenoyl)-1H-pyrrole, 7 mL (0.087 mole) of chloroacetyl chloride and 7.7 g (0.12 mole) of aluminum chloride in 500 mL of 1,2-dichloroethane was stirred at room temperature for 1 h. The reaction mixture was heated to reflux for 3 h. Another 7 g of aluminum chloride was added and refluxing continued for 1 h. After cooling, the reaction mixture was poured into 2 N HCl/ice, the organics were separated, washed with water, NaHCO3, water, brine and dried (Na2SO4). The solvent was evaporated in vacuo and recrystallized from toluene to give 13.9 g (81%) of 2-chloro-1-[4-(2-naphthalenoyl)-1H-pyrrol-2-yl]ethanone. mp 175-177° C. CIMS m/z 299 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.4 (Ar, 1H); 8.0-7.85 (Ar, 4H); 7.7-7.5 (Ar, 4H); 4.6 (s, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 h
  3. temperaturerefluxing
  4. waitcontinued for 1 h
  5. temperatureAfter cooling
  6. customthe organics were separated
  7. washwashed with water, NaHCO3, water, brine
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was evaporated in vacuo
  10. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e849e74b02424009a8e6ffe6745a1bdf
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

Loading…