Hydrochloric Acid → HCID 86733259, compound

HRID 1275262Notes

Reaction equation

HRID 1275262 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5](Cl)=[O:6].[Cl-:12].[Al+3].[Cl-].[Cl-].[CH3:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][C:23]#[N:24].Cl>ClCCCl>[Cl:12][C:3]1[CH:2]=[C:10]([CH3:11])[CH:9]=[CH:8][C:4]=1[C:5]([C:21]1[N:17]([CH3:16])[C:18]([CH2:22][C:23]#[N:24])=[CH:19][CH:20]=1)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 6451240Aluminum(III) ChlorideHCID 184242113-Chloro-4-methylbenzoyl chloride

Product 1

HCID 86733259HCID 86733259, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

21.4 grams (0.114 mole) of 3-chloro-4-methylbenzoylchloride is added to a suspension of 15.2 g. (0.114 mole) aluminum chloride in 50 ml. 1,2-dichloroethane. The resulting solution is added dropwise to a chilled solution of 13.7 g. (0.114 mole) of 1-methylpyrrole-2-acetonitrile in 50 ml. 1,2-dichloroethane. After the addition is complete, the mixture is stirred for ten minutes at room temperature, and then heated to reflux for three minutes. It is poured into ice acidified with dilute HCl. The organic phase is separated and washed consecutively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution. It is then dried over anhydrous magnesium sulfate, and the solvent evaporated off. A white solid, 5-(3'-chloro-p-toluoyl)-1-methyl pyrrole-2-acetonitrile, precipitates from the resulting oily residue upon trituration with methanol which is purified by recrystallization from methanol, m.p. 116-118° C. Analysis: Calcd. for C15H13ClN2O: N, 10.26%. Found: N, 10.38%.

Workup

  1. additionThe resulting solution is added dropwise to a chilled solution of 13.7 g
  2. additionAfter the addition
  3. temperatureheated
  4. temperatureto reflux for three minutes
  5. additionIt is poured into ice
  6. customThe organic phase is separated
  7. washwashed consecutively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution
  8. dry with materialIt is then dried over anhydrous magnesium sulfate
  9. customthe solvent evaporated off
  10. customA white solid, 5-(3'-chloro-p-toluoyl)-1-methyl pyrrole-2-acetonitrile, precipitates from the resulting oily residue upon trituration with methanol which
  11. customis purified by recrystallization from methanol, m.p. 116-118° C

Sources & evidence

ORD record
ord-1d4128768bbf45f891339fe12c708d60
Source dataset
uspto-grants-2000_12
Patent number
US06160003

Reaction notes

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