Dimethylformamide → HCID 69521475, compound

HRID 856470Notes

Reaction equation

HRID 856470 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]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][C:21]([C:28](O)=[O:29])=[CH:20][C:19]=3[CH:31]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].CN(C=O)C.S(Cl)(Cl)=O.[N:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[S:47][CH2:48][C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=1>C1COCC1.O.C(N(CC)CC)C>[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]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:22][C:21]([C:28]([NH:53][C:52]4[CH:54]=[CH:55][C:49]([CH2:48][S:47][C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][N:41]=5)=[CH:50][CH:51]=4)=[O:29])=[CH:20][C:19]=3[CH:31]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 114301667-[4-(2-Butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acidHCID 284023404-[(Pyridin-2-ylsulfanyl)methyl]aniline

Product 1

HCID 69521475HCID 69521475, compoundYield 38.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

7-[4-(2-butoxyethoxy)phenyl]-1-propyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (1.0 g) was dissolved in THF (20 ml), DMF (2 droplets) was added to the solution, thionyl chloride (0.34 ml) was added to the solution, and the solution was stirred at room temperature for 1 hour. The solution was added dropwise to the solution of 4-[(2-pyridinylsulfanyl)methyl]aniline (0.56 g) and triethylamine (1.97 ml) in THF (20 ml) under ice-cooling at room temperature and the mixture was stirred for 2 hours. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[(2-pyridinylsulfanyl)methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 180) (0.56 g).

Workup

  1. additionwas added to the solution
  2. temperaturecooling at room temperature
  3. stirringthe mixture was stirred for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-21a7ad15096d41b5a3bdaf57c564c7cd
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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