Calcium Carbonate → Methyl 3-chloro-1-methyl-5-(p-toluoyl)pyrrole-2-acetate

HRID 2071674Notes

Reaction equation

HRID 2071674 reaction equation
[Cl:1]Cl.[CH3:3][N:4]1[C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=[C:5]1[CH2:18][C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[Ca+2]>C(Cl)(Cl)Cl>[Cl:1][C:6]1[CH:7]=[C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[O:10])[N:4]([CH3:3])[C:5]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 24526ChlorineHCID 118468Methyl 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetate

Product 1

HCID 21411867Methyl 3-chloro-1-methyl-5-(p-toluoyl)pyrrole-2-acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 4.26g (0.06 mole) of chlorine in 75 ml. of chloroform is added rapidly to a mixture of 16.2g. (0.06 mole) of methyl 1-methyl-5-(p-toluoyl)- pyrrole-2-acetate, 16g (0.12 mole) of calcium carbonate, and 0.48g. (0.003 mole) of ferric chloride in 75 ml. of chloroform. The temperature rose somewhat. After an hour, when the chlorine has been consumed, the solids are removed by filtration and the filtrate is evaporated in vacuo to yield a red oil. The oil is chromatographed on 2lb. of Silica (Mallinkrodt SILIC-AR CC-4) 100-200 mesh and eluted successively with hexane, benzene, and chloroform. The first compound-bearing fraction is eluted with chloroform. The solvent is evaporated and the residue is recrystallized from methanol to give white crystalline methyl 3-chloro-1-methyl-5-(p-toluoyl)pyrrole-2-acetate; m.p. 144°-146° C.

Workup

  1. waitAfter an hour
  2. customwhen the chlorine has been consumed
  3. customthe solids are removed by filtration
  4. customthe filtrate is evaporated in vacuo
  5. customto yield a red oil
  6. customThe oil is chromatographed on 2lb
  7. washof Silica (Mallinkrodt SILIC-AR CC-4) 100-200 mesh and eluted successively with hexane, benzene, and chloroform
  8. washThe first compound-bearing fraction is eluted with chloroform
  9. customThe solvent is evaporated
  10. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-427ecf13a7e2448c897a17ed4380e8cb
Source dataset
uspto-grants-1977_09
Patent number
US04048191

Reaction notes

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