Acetic Acid → HCID 13457722, compound

HRID 280130Notes

Reaction equation

HRID 280130 reaction equation
Br.[CH3:2][N:3]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[C:4](=[O:7])[CH2:5][NH2:6].C(O)(=O)C>C(O)(C)C>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]1[C:9]2[N:8]([CH:12]=[CH:11][CH:10]=2)[N:3]([CH3:2])[C:4](=[O:7])[CH2:5][N:6]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13457758HCID 13457758, compound

Product 1

HCID 13457722HCID 13457722, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution containing 1-(N-methyl-aminoacetamido)-2-(2-chlorobenzoyl)pyrrole hydrobromide (12.6 g, 43.4 mmol) and glacial acetic acid (15 g, 0.25 mol) in 100 ml of isopropanol was refluxed under nitrogen for 12 hours and thereafter evaporated to an oil. This oil was flash chromatographed (silica, 4:1 ethyl acetate-hexane) to give 3.2 g (27%) of crystals, m.p. 132°-134°. This was combined with 0.5 g from an earlier run and recrystallized from acetone to give 3.5 g of crystals, m.p. 132°-133.5°.

Workup

  1. temperaturewas refluxed under nitrogen for 12 hours
  2. customevaporated to an oil
  3. customchromatographed (silica, 4:1 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-7c7d4d8613714047b2c5b4fabe14f8df
Source dataset
uspto-grants-1986_05
Patent number
US04588727

Reaction notes

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