Water → HCID 53791231, compound

HRID 2294845Notes

Reaction equation

HRID 2294845 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 exract 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 exract 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-81d4760c9ded41418afda4c3ac79458d
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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