Water → HCID 53791231, compound

HRID 1734070Notes

Reaction equation

HRID 1734070 reaction equation
[C:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[C:12]([C:14](=O)[CH2:15][Cl:16])[S:13][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].O>C([SiH](CC)CC)C.FC(F)(F)C(O)=O>[C:1]([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[C:12]([CH2:14][CH2:15][Cl:16])[S:13][C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 21472015HCID 21472015, compound

Product 1

HCID 53791231HCID 53791231, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Procedure

A mixture of 2.1 g of 7-acetyl-2-chloroacetyl-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepine in 5.4 ml of triethylsilane and 15 ml of trifluoroacetic acid was stirred at room temperature for 12 hours. The mixture was poured into water, made alkaline and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by column chromatography on a silica gel to give 1.8 g of 7-acetyl-2-chloroethyl-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepine as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on a silica gel

Sources & evidence

ORD record
ord-489694cad763478fbfb7fb079616a29d
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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