4-Chlorobutyryl chloride → 7-(4-chlorobutyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one

HRID 1734035Notes

Reaction equation

HRID 1734035 reaction equation
[S:1]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5](=[O:11])[NH:4][CH2:3][CH2:2]1.[Cl:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[Cl:12][CH2:13][CH2:14][CH2:15][C:16]([C:9]1[S:8][C:7]2[S:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[C:6]=2[CH:10]=1)=[O:17]

Participants

5

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 43659423,4-dihydrothieno[3,2-f][1,4]thiazepin-5(2H)-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 214720567-(4-chlorobutyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-oneYield 59%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture of 13 g of 2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one and 21.5 g of 4-chlorobutyryl chloride in 200 ml of dichloroethane was added 21.5 g of aluminum chloride under cooling and the mixture was stirred for 3 hours. The mixture was poured into ice-cold water and extracted with chloroform. The organic layer was washed with saline solution, dried over magnesium sulfate and concentrated. The residue was recrystallized from ethanol to give 12 g of 7-(4-chlorobutyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one as white crystals, m.p. 124°-125° C.

Workup

  1. temperatureunder cooling
  2. additionThe mixture was poured into ice-cold water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saline solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-1e13a71674284da2bf458f42cd064284
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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