Phenylacetyl chloride → 4,9-Dihydro-4-phenylacetyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1863156Notes

Reaction equation

HRID 1863156 reaction equation
[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5]2.[C:16]1([CH2:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1C=CC=CC=1>[C:16]1([CH2:22][C:23]([N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9](=[O:11])[C:10]3=[CH:1][S:2][CH:3]=[C:4]23)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7679Phenylacetyl chlorideHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 203922494,9-Dihydro-4-phenylacetyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A reaction mixture comprising 6.48 g. of 4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 25 g. of phenylacetyl chloride in 100 ml. of benzene is refluxed with stirring for 3 hours. The mixture is evaporated to an amber oil, combined with 100 ml. of ethanol and 6 ml. of 5 N sodium hydroxide and allowed to stand at room temperature for one hour. This solution is evaporated to an oily residue which is triturated with water and filtered, giving the desired product as pale pink crystals, mp. 165°-168° C.

Workup

  1. customThe mixture is evaporated to an amber oil
  2. waitto stand at room temperature for one hour
  3. customThis solution is evaporated to an oily residue which
  4. customis triturated with water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-bff9e9a0063c4c5f86a50e2699e56d32
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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