Acetaldehyde → HCID 178463263, compound

HRID 1595403Notes

Reaction equation

HRID 1595403 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:11]([C:13]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH:34](=O)[CH3:35].[BH4-].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.CO>[CH2:34]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:11]([C:13]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1)[CH3:35]

Participants

8

Reactant 5

HCID 177AcetaldehydeHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178489037HCID 178489037, compound

Product 1

HCID 178463263HCID 178463263, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-(4-Aminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (1.0 g) obtained in Example 48 was dissolved in a mixed solvent of tetrahydrofuran and methanol, and added to a solution of 4N sulfuric acid (0.2 ml) and acetaldehyde (0.2 ml) in tetrahydrofuran. To the solution was added sodium borohydride (0.13 g) and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added a saturated aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with saturated brine, dried and concentrated. The residue was purified by silica gel chromatography using, as a mobile phase, chloroform/ethyl acetate=100:1 to give 2-(4-ethylaminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (1.2 g). This was converted to hydrochloride to give 2-(4-ethylaminophenyl)-5-(4-methoxy-phenyl)-N-(2-thiazolyl)imidazole-4-carboxamide hydrochloride (0.48 g), melting point 250° C. or above.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate phase was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0c6e2a002de14539be3eebf7392967fc
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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