HCID 10512214, compound → HCID 14650082, compound

HRID 1722737Notes

Reaction equation

HRID 1722737 reaction equation
C[O-].[Na+].[CH3:4][N:5]([CH3:16])[C:6]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)([CH2:9][CH3:10])[CH2:7][OH:8].[NH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22](OC)=[O:23])=[C:20]([O:28][CH3:29])[C:19]=1[Cl:30]>C1(C)C=CC=CC=1>[NH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:8][CH2:7][C:6]([N:5]([CH3:4])[CH3:16])([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH2:9][CH3:10])=[O:23])=[C:20]([O:28][CH3:29])[C:19]=1[Cl:30]

Participants

5

Reactant 3

HCID 10512214HCID 10512214, compoundHCID 10942334Sodium MethoxideHCID 14994174HCID 14994174, compound

Product 1

HCID 14650082HCID 14650082, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Sodium methoxide (0.4 g) is added to a solution of 2-dimethylamino-2-(2-thienyl)-1-butanol (7.5 g) and methyl 4-amino-3-chloro-2-methoxybenzoate (16.2 g) in toluene (150 ml) and the mixture is stirred at 110° C. for 96 hours while removing methanol which is produced during the reaction. After cooling, the mixture is washed with water, dried and concentrated to remove solvent. The residue is purified by silica gel column chromatography (solvent, chloroform:ethanol=50:1), whereby 2-dimethylamino-2-(2-thienyl)butyl 4-amino-3-chloro-2-methoxybenzoate (3.6 g) is obtained as colorless crystals.

Workup

  1. customwhile removing methanol which
  2. customis produced during the reaction
  3. temperatureAfter cooling
  4. washthe mixture is washed with water
  5. customdried
  6. concentrationconcentrated
  7. customto remove solvent
  8. customThe residue is purified by silica gel column chromatography (solvent, chloroform:ethanol=50:1)

Sources & evidence

ORD record
ord-c6fb84f01ed94429835860c70a2378b8
Source dataset
uspto-grants-1989_08
Patent number
US04857543

Reaction notes

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