Methylamine → HCID 18707270, compound

HRID 1489271Notes

Reaction equation

HRID 1489271 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][CH2:27][O:28][CH3:29])=[C:20]([C:30]([O:32][CH3:33])=[O:31])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[CH3:34][NH2:35].B.[Na]>CO>[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:28][CH3:29])=[C:20]([C:30]([O:32][CH3:33])=[O:31])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 18707338HCID 18707338, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 18707270HCID 18707270, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

In 30 ml of methanol was dissolved 500 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-methoxymethoxy-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-methylaminomethylphenyl)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-409bccd94734409e9b6993ef4b46c634
Source dataset
uspto-grants-1997_10
Patent number
US05677319

Reaction notes

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