1,3-Thiazole-5-carbaldehyde → Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 587064Notes

Reaction equation

HRID 587064 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH2:20][C:19]=3[CH:29]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[S:30]1[C:34]([CH:35]=O)=[CH:33][N:32]=[CH:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:35][C:34]4[S:30][CH:31]=[N:32][CH:33]=4)[CH2:23][CH2:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][C:19]=3[CH:29]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 27735771,3-Thiazole-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 69749802Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-benzazepine-4-carboxylate

Product 1

HCID 22329006Methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylateYield 79.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 1,2-dichloroethane (15 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-1-benzazepine-4-carboxylate (0.50 g). To the solution were added 1,3-thiazole-5-carbaldehyde 10.43 g) and sodium triacetoxyborohydride (0.80 g), and the mixture was stirred at room temperature for 24 hours. To the mixture was added sodium triacetoxyborohydride (0.27 g), and the mixture was stirred for 6 hours. The solvent was removed under reduced pressure, the resulting residue was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=3/2→2/3) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(1,3-thiazol-5-ylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (0.50 g).

Workup

  1. stirringthe mixture was stirred for 6 hours
  2. customThe solvent was removed under reduced pressure
  3. additionthe resulting residue was added to water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=3/2→2/3)

Sources & evidence

ORD record
ord-20fab3757f764e6cb93121b37c4e138d
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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