Acetyl chloride → HCID 20248790, compound

HRID 1285301Notes

Reaction equation

HRID 1285301 reaction equation
[O:1]=[CH:2][C:3]([Cl:6])([Cl:5])[Cl:4].C(N(CC)CC)C.[Cl:14][C:15]1[CH:20]=[C:19](Cl)[CH:18]=[CH:17][C:16]=1[C:22]1[C:26]([C:27]#[N:28])=[CH:25][NH:24][CH:23]=1.C([Cl:32])(=O)C.[O:33]1CC[CH2:35][CH2:34]1>CN(C)C1C=CN=CC=1>[C:34]([O:1][CH:2]([N:24]1[CH:25]=[C:26]([C:27]#[N:28])[C:22]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([Cl:32])[C:15]=2[Cl:14])=[CH:23]1)[C:3]([Cl:6])([Cl:5])[Cl:4])(=[O:33])[CH3:35]

Participants

7

Reactant 5

HCID 6367Acetyl chlorideHCID 6407ChloralHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 202487984-(2,4-Dichlorophenyl)-1H-pyrrole-3-carbonitrile

Product 1

HCID 20248790HCID 20248790, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
25 °C

Procedure

1.2 ml of chloral and 1.8 ml of triethylamine are added dropwise in succession to 2.4 g of 3-(2,4-dichlorophenyl)-4-cyanopyrrole in 50 ml of tetrahydrofuran. The reaction mixture is stirred for 11/2 hours at 25° C., then 0.1 g of 4-dimethylaminopyridine is added and the mixture is cooled to -10° C. A solution of 0.9 ml of acetyl chloride in 10 ml of tetrahydrofuran is added very slowly dropwise at -10° to -5° C. and the reaction mixture is subsequently stirred for 30 minutes at 0° C. and then for 1 hour at room temperature, and filtered. The filtrate is concentrated and the residue is dissolved in diethyl ether. The ethereal solution is washed twice with a semi-saturated solution of sodium chloride, dried over sodium sulfate, and filtered. The filtrate is concentrated and the crude product is recrystallised from diethyl ether/petroleum ether to give colourless crystals of the title compound with a melting point of 111°-113° C.

Workup

  1. temperaturethe mixture is cooled to -10° C
  2. stirringthe reaction mixture is subsequently stirred for 30 minutes at 0° C.
  3. waitfor 1 hour at room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated
  6. dissolutionthe residue is dissolved in diethyl ether
  7. washThe ethereal solution is washed twice with a semi-saturated solution of sodium chloride
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate is concentrated
  11. customthe crude product is recrystallised from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-539259fb52f143ae974dbad62559c936
Source dataset
uspto-grants-1986_01
Patent number
US04567052

Reaction notes

Loading…