Hydrochloric Acid → HCID 18424235, compound

HRID 1275264Notes

Reaction equation

HRID 1275264 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:17][N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24]#[N:25].Cl>ClCCCl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([C:22]2[N:18]([CH3:17])[C:19]([CH2:23][C:24]#[N:25])=[CH:20][CH:21]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 905011H-Pyrrole-2-acetonitrile, 1-methyl-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424235HCID 18424235, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

A solution of 46.4 g. (0.25 mole) of p-nitrobenzoyl chloride in 100 ml. 1,2-dichloroethane is added portionwise to a suspension of 32.2 g. (0.25 mole) aluminum cloride in 100 ml. 1,2-dichloroethane. This mixture is added dropwise to a chilled solution of 30.0 g. (0.25 mole) 1-methylpyrrole-2-acetonitrile in 100 ml. 1,2-dichloroethane. After the addition is complete, the mixture is stirred for twenty minutes at room temperature and then refluxed for four minutes. It is poured into ice acidified with 2N hydrochloric acid. The organic phase is separated and washed successively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution. It is then dried over magnesium sulfate and the solvent evaporated in vacuo. The resulting semi-solid residue is triturated with cold methanol from which the product, 5-(p-nitrobenzoyl)-1-methylpyrrole-2-acetonitrile, crystallizes. It is removed by filtration and purified by recrystallization from acetone, m.p. 167-169° C.

Workup

  1. additionThis mixture is added dropwise to a chilled solution of 30.0 g
  2. additionAfter the addition
  3. temperaturerefluxed for four minutes
  4. additionIt is poured into ice
  5. customThe organic phase is separated
  6. washwashed successively with N,N-dimethyl-1,3-propanediamine, 3N hydrochloric acid and saturated sodium chloride solution
  7. dry with materialIt is then dried over magnesium sulfate
  8. customthe solvent evaporated in vacuo
  9. customThe resulting semi-solid residue is triturated with cold methanol from which the product, 5-(p-nitrobenzoyl)-1-methylpyrrole-2-acetonitrile
  10. customcrystallizes
  11. customIt is removed by filtration
  12. custompurified by recrystallization from acetone, m.p. 167-169° C.

Sources & evidence

ORD record
ord-1777309c9b124260bdcec5071578e80d
Source dataset
uspto-grants-2000_12
Patent number
US06160003

Reaction notes

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