Dimethylformamide → HCID 20376215, compound

HRID 2052560Notes

Reaction equation

HRID 2052560 reaction equation
[NH2:1][CH2:2][C:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)([OH:7])[CH2:4][CH2:5][CH3:6].CN(C)[CH:20]=[O:21].C(C1NC=CN=1)(C1NC=CN=1)=O>O1CCCC1>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:3]2([CH2:4][CH2:5][CH3:6])[O:7][C:20](=[O:21])[NH:1][CH2:2]2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 20376207HCID 20376207, compound

Product 1

HCID 20376215HCID 20376215, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.35 mmol of 5-amino-4-(3,4-dimethoxyphenyl)-4-pentanol is dissolved in 10 ml. of absolute dimethylformamide and reacted with 18.3 mmol of 98% strength carbonyl diimidazole in 100 ml. of absolute tetrahydrofuran for 4 days at room temperature under the exclusion of moisture. After the solvent has been distilled off, the residue is taken up in ethyl acetate, extracted twice with 1 N hydrochloric acid, and washed neutral with saturated sodium chloride solution. The thus-obtained oil is purified by way of a silica gel column (350 g.) in a chloroform/methanol system 30:1. The product is 5-(3,4-dimethoxyphenyl)-5-propyl-2-oxazolidinone in an 81.7% yield in the form of an oil.

Workup

  1. distillationAfter the solvent has been distilled off
  2. extractionextracted twice with 1 N hydrochloric acid
  3. washwashed neutral with saturated sodium chloride solution
  4. customThe thus-obtained oil is purified by way of a silica gel column (350 g.) in a chloroform/methanol system 30:1

Sources & evidence

ORD record
ord-f6fc2ec950494c2fb485ae5fe818d0dd
Source dataset
uspto-grants-1980_01
Patent number
US04186129

Reaction notes

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