Methanol → HCID 18707270, compound

HRID 1699581Notes

Reaction equation

HRID 1699581 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH:24]=O)[C:21]([O:26][CH3:27])=[C:20]([C:28]([O:30][CH3:31])=[O:29])[C:19]=3OC)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[CH3:34][NH2:35].B.[Na].[CH3:38][OH:39]>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:24][NH:35][CH3:34])[C:21]([O:26][CH2:27][O:39][CH3:38])=[C:20]([C:28]([O:30][CH3:31])=[O:29])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 86751014HCID 86751014, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 18707270HCID 18707270, compound

Conditions

Temperature
70 °C

Procedure

In 30 ml of methanol was dissolved 500 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxy-methoxy-5-formylphenyl)thiazole. Thereto was added 3 ml of a 30% methylamine solution. The mixture was stirred at room temperature for 14 hours and at 70° C. for 1 hour. Thereto was added 530 ml of sodium boron hydride with stirring under ice-cooling. The mixture was stirred at room temperature for 3 hours. The solvent was removed from the reaction mixture by distillation. The residue was mixed with 40 ml of ethyl acetate and 20 ml of water, and phase separation was conducted. The organic layer was washed with 10 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was subjected to silica gel chromatography (eluent: dichloromethane/methanol=49/1 by v/v). From the eluate was obtained 150 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxymethoxy-5-methylaminomethyl-phenyl)thiazole.

Workup

  1. stirringwith stirring under ice-
  2. temperaturecooling
  3. stirringThe mixture was stirred at room temperature for 3 hours
  4. customThe solvent was removed from the reaction mixture by distillation
  5. additionThe residue was mixed with 40 ml of ethyl acetate and 20 ml of water, and phase separation
  6. washThe organic layer was washed with 10 ml of a saturated aqueous sodium chloride solution
  7. customdried
  8. distillationsubjected to distillation
  9. customto remove the solvent

Sources & evidence

ORD record
ord-7d0f09952aa5479b98ccd96d7a6e37b8
Source dataset
uspto-grants-2002_02
Patent number
USRE037556E1

Reaction notes

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