Triethylamine → HCID 19029049, compound

HRID 2255988Notes

Reaction equation

HRID 2255988 reaction equation
[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.[CH2:18]([O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)[CH2:19][CH2:20][CH3:21]>ClCCl.O>[CH2:18]([O:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[S:1][CH:2]=[CH:3][C:4]2=3)=[O:28])=[CH:30][CH:31]=1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1185614-Butoxybenzoyl chlorideHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

Product 1

HCID 19029049HCID 19029049, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a chilled (0° C.) solution of 0.306 g of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine and 417 μl of triethylamine is added 474 μl of 4-(n-butoxy)benzoyl chloride. The mixture is stirred for 3 days at room temperature, diluted with 50 ml of dichloromethane and 20 ml of water. The organic layer is separated and washed with 20 ml each of 2N citric acid, 1M NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate, the pad washed with CH2Cl2 and the filtrate evaporated. The residue is crystallized from hexane containing a small amount of ethyl acetate. The crystals (0.585 g) are purified by chromatography on silica gel plates with hexane-ethyl acetate (2:1) as solvent to give 0.40 g of crystals (from ethyl acetate-hexane), m.p. 87° C. to 90° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with 20 ml each of 2N citric acid, 1M NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. washthe pad washed with CH2Cl2
  6. customthe filtrate evaporated
  7. customThe residue is crystallized from hexane containing a small amount of ethyl acetate
  8. customThe crystals (0.585 g) are purified by chromatography on silica gel plates with hexane-ethyl acetate (2:1) as solvent

Sources & evidence

ORD record
ord-110ca7a158e84134900fdc4dda460a30
Source dataset
uspto-grants-1997_08
Patent number
US05654297

Reaction notes

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