Ammonia → HCID 18424383, compound

HRID 1585592Notes

Reaction equation

HRID 1585592 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 an oily residue which 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 an oily residue which
  9. customcrystallizes
  10. customThe solid is recrystallized successively from cyclohexane and methanol

Sources & evidence

ORD record
ord-efb928969caa436e926e97798b2d215b
Source dataset
uspto-grants-1999_08
Patent number
US05939417

Reaction notes

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