Chloroacetyl chloride → HCID 13472304, compound

HRID 1248041Notes

Reaction equation

HRID 1248041 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl[CH2:14][C:15](Cl)=[O:16].[Cl-].[Cl-].[Cl-].[Al+3].[CH2:22]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C.ClCCl.C(=S)=S>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:15](=[O:16])[CH2:14][N:29]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 7656DibenzylamineHCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13472304HCID 13472304, compoundYield 85.9%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 6348Carbon DisulfideSolvent

Conditions

Temperature
40 °C

Procedure

1-Acetylindoline (16.1 g, 0.1 mol) and chloroacetylchloride (14.0 g, 9.6 mL, 0.12 mol) were added to carbon disulfide (200 mL) and heated to 40° C. Aluminium trichloride (42 g, 0.315 mol) was added portionwise to the mechanically stirred solution. After the addition was complete, the mixture was refluxed for 2 hours. The carbon disulfide was decanted and the remaining traces of carbon disulfide were evaporated using a stream of nitrogen while stirring the mixture (1 hour). Ice was added (exothermic!) to the dark green slurry with stirring under nitrogen. The ice mixture was stirred until a white homogenous mixture was obtained. The solid (32 g) was collected, washed with water, dried in air and reacted as such with dibenzylamine (60 g, 0.31 mol) at reflux temperature in dry acetonitrile (650 mL) overnight. The resulting mixture was cooled (10° C.) and dichloromethane (650 mL) was added. The precipitate was filtered, and the filtrate was concentrated to dryness. The residue was triturated with diethyl ether to afford a yellow solid (34.24 g) of 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-[bis(phenylmethyl)amino]-ethanone: mp 130° C. (crystallized from ethyl acetate) and NMR (CDCl3) δ 2.2(s, 3H), 3.1(t, 2H), 3.7(s, 6H), 4.05(t, 2H), 7.4(m, 13H).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 2 hours
  3. customThe carbon disulfide was decanted
  4. customthe remaining traces of carbon disulfide were evaporated
  5. additionIce was added (exothermic!) to the dark green slurry
  6. stirringwith stirring under nitrogen
  7. stirringThe ice mixture was stirred until a white homogenous mixture
  8. customwas obtained
  9. customThe solid (32 g) was collected
  10. washwashed with water
  11. additionwas added
  12. filtrationThe precipitate was filtered
  13. concentrationthe filtrate was concentrated to dryness
  14. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-3cabaf4df88e4382a88124e12dbd3977
Source dataset
uspto-grants-1985_06
Patent number
US04521606

Reaction notes

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