Chlorotrimethylsilane → HCID 53873845, compound
Reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1.C(N(CC)CC)C.Cl[Si](C)(C)C.[Cl:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32]>ClCCl>[Cl:27][CH2:28][CH2:29][CH2:30][C:31]([N:10]([C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH:2]=1)[CH2:11][C:12]([OH:14])=[O:13])=[O:32]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A solution of 621 mg (3 mM) of 3-benzothienylglycine in 15 ml of dichloromethane containing 0.92 ml (6.6 mM) of triethylamine and 717 mg of chlorotrimethylsilane was heated at 50° C. and stirred for thirty minutes and then cooled to 5° C. A solution of 0.336 ml (3 mM) of 4-chlorobutyryl chloride in 5 ml of dichloromethane was added dropwise to the reaction mixture and stirring was continued at 5° C. for one hour following the addition. The reaction mixture was warmed to 25° C. and stirred for an additional hour. The reaction mixture was next washed twice with 10 ml portions of water, dried, and the solvent was removed by evaporation to give an oil. The oil was crystallized from 0.7 ml of acetone and 2.7 ml of water, and recrystallized from ethyl acetate to afford 150 mg of N-(3-chloropropylcarbonyl)-3-benzothienylglycine. m.p. 167°-168° C.
Workup
- stirringstirring
- additionthe addition
- temperatureThe reaction mixture was warmed to 25° C.
- stirringstirred for an additional hour
- washThe reaction mixture was next washed twice with 10 ml portions of water
- customdried
- customthe solvent was removed by evaporation
- customto give an oil
- customThe oil was crystallized from 0.7 ml of acetone and 2.7 ml of water
- customrecrystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-483dcc504e5348c2a4e8e09c9df13f53
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04492693
Reaction notes
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