Sulfuryl chloride → 3-chloro-4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1702451Notes

Reaction equation

HRID 1702451 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][CH2:7][C:8]([N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][C:13](=[O:21])[C:12]2=[CH:22][S:23][CH:24]=[C:11]12)=[O:9]>C(Cl)Cl>[Cl:4][C:24]1[S:23][CH:22]=[C:12]2[C:13](=[O:21])[NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:10]([C:8](=[O:9])[CH2:7][Cl:6])[C:11]=12

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 200638994-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 205037673-chloro-4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 ml of sulfuryl chloride in 100 ml methylene chloride are added dropwise to a solution of 12 g of 4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one in 300 ml of methylene chloride at 20° C. The mixture is left to stand at room temperature for a further 12 hours and is then extracted by shaking it with sodium bicarbonate solution and washing it with water; the organic phase is dried and concentrated. The residue is made to crystallize with a little methanol. 7 g of 3-chloro-4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one is thus obtained, m. 214° to 216° C. (acetonitrile).

Workup

  1. waitThe mixture is left
  2. extractionis then extracted
  3. washwashing it with water
  4. customthe organic phase is dried
  5. concentrationconcentrated
  6. customto crystallize with a little methanol

Sources & evidence

ORD record
ord-7b48a208058b4fa5b6ea563081860229
Source dataset
uspto-grants-1983_04
Patent number
US04381301

Reaction notes

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