Dimethyl Sulfate → [4-Chloro-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetonitrile

HRID 2071680Notes

Reaction equation

HRID 2071680 reaction equation
[CH3:1]C(C)[O-].[Na+].[Na].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:22][C:23]#[N:24])[NH:11][C:12]=1[C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1.S(OC)(OC)(=O)=O>C(O)(C)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:22][C:23]#[N:24])[N:11]([CH3:1])[C:12]=1[C:13](=[O:21])[C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6497Dimethyl Sulfate2×HCID 5360545SodiumHCID 109204432-Propanol, sodium salt (1:1)HCID 22765717[4-Chloro-5-(4-chlorobenzoyl)-1H-pyrrol-2-yl]acetonitrile

Product 1

HCID 21411896[4-Chloro-5-(4-chlorobenzoyl)-1-methyl-1H-pyrrol-2-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a refluxing solution of sodium isopropoxide in isopropanol (prepared by refluxing 0.69 g. (0.030 mole) of sodium in 70 ml. of isopropanol) is added 7.0 g. (0.025 mole) of 4-chloro-5-(p-chlorobenzoyl)-pyrrole- 2-acetonitrile prepared according to Example VIII, after which a solution of 3.78 g. (0.030 mole) of dimethyl sulfate in 10 ml. of isopropanol is added dropwise. When addition of the dimethyl sulfate solution is complete, the whole is refluxed for a half-hour and then poured into 1 liter of ice water. Filtration of the resulting mixture yields a grey solid, which is washed well with water and is then chromatographed with benzene on alumina. The chromatographed material is finally recrystallized from isopropanol to yield 4-chloro-5-(p-chlorobenzoyl)-1-methyl- pyrrole-2-acetonitrile as a beige solid; m.p. 139°-142° C.

Workup

  1. temperaturethe whole is refluxed for a half-hour
  2. filtrationFiltration of the resulting mixture
  3. customyields a grey solid, which
  4. washis washed well with water
  5. customis then chromatographed with benzene on alumina
  6. customThe chromatographed material is finally recrystallized from isopropanol

Sources & evidence

ORD record
ord-2793ea191d054ad8925d8cb99e33e666
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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