Triethylamine → HCID 86746740, compound

HRID 1033560Notes

Reaction equation

HRID 1033560 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH:8]([CH3:12])[C:9]([OH:11])=O.S(Cl)(Cl)=O.[Cl:17][C:18]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:19]=1[NH2:20].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(Cl)Cl>[O:7]=[C:4]1[CH:5]=[CH:6][C:2](=[O:1])[N:3]1[CH:8]([CH3:12])[C:9]([NH:20][C:19]1[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=1[Cl:17])=[O:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111232,4-DichloroanilineHCID 24386Thionyl ChlorideHCID 3199362-(2,5-dioxopyrrol-1-yl)propanoic acid

Product 1

HCID 86746740HCID 86746740, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A suspension of DL-2,5-dioxo-α-methyl-3-pyrroline-1-acetic acid (1.5 g, 0.0086 mol) in toluene is treated with thionyl chloride (1.28 mL, 0.0176 mol), warmed to 50° C., stirred for 21/2 hours, cooled and concentrated in vacuo to yield a yellow oil. The oil is dissolved in methylene chloride and added to a solution of 2,4-dichloroaniline (1.54 g, 0.0086 mol) and triethylamine (1.32 mL, 0.0094 mol) in methylene chloride under nitrogen at 0° C. The reaction mixture is stirred for 1 hour at room temperature and concentrated in vacuo to give a residue. The residue is flash chromatographed using hexane/ethyl acetate (80/20) as eluent on silica gel to give the title compound as a pale yellow solid (0.94 g, 35%, mp 131° C.), identified by 1HNMR, CIMS and IR analysis.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. customto yield a yellow oil
  4. stirringThe reaction mixture is stirred for 1 hour at room temperature
  5. concentrationconcentrated in vacuo
  6. customto give a residue
  7. customchromatographed

Sources & evidence

ORD record
ord-d10cbc23e7ba43e3af1f893c41fa30d2
Source dataset
uspto-grants-1994_05
Patent number
US05310937

Reaction notes

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