Ammonia → HCID 18424383, compound

HRID 1606147Notes

Reaction equation

HRID 1606147 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[NH2-].[Na+].N.[CH3:25]I.[Cl-].[NH4+].Cl>CCOCC>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH:14]([CH3:25])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24533Sodium amideHCID 25517Ammonium ChlorideHCID 18424207HCID 18424207, compound

Product 1

HCID 18424383HCID 18424383, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 6.68 g. (0.0219 mole) of ethyl 5-(p-chlorobenzoyl)-1-methylpyrrole-2-acetate in 50 ml. of ether is added to a solution of 0.94 g. (0.024 mole) of sodamide in about 150 ml. of liquid ammonia at -33°C. The mixture is allowed to reflux for 15 minutes and 3.10 g. (0.0219 mole) of methyl iodide is added. The mixture is stirred for one hour; then the ammonia is allowed to boil off. Ether and enough ammonium chloride to neutralize any anion are added. The mixture is poured into dilute hydrochloric acid and the ether solution is separated and washed with sodium bisulfite solution, sodium bicarbonate solution and brine. It is dried over anhydrous magnesium sulfate and evaporated to give about 6.8 g. of an oily residue whch crystallizes upon standing. The solid is recrystallized successively from cyclohexane and methanol to give a white crystalline solid, ethyl 5-(p-chlorobenzoyl)-α-methyl-1-methylpyrrole-2-acetate, m.p. 67°-68°C.

Workup

  1. customat -33°C
  2. temperatureto reflux for 15 minutes
  3. additionare added
  4. customthe ether solution is separated
  5. washwashed with sodium bisulfite solution, sodium bicarbonate solution and brine
  6. dry with materialIt is dried over anhydrous magnesium sulfate
  7. customevaporated
  8. customto give about 6.8 g
  9. customof an oily residue whch crystallizes
  10. customThe solid is recrystallized successively from cyclohexane and methanol

Sources & evidence

ORD record
ord-a3439d34ca2943fe8bd0f10e272c8775
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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