Potassium Carbonate → HCID 19881116, compound

HRID 847395Notes

Reaction equation

HRID 847395 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][C:9]2[S:13][C:14]([CH3:16])=[CH:15][C:8]=2[C:7]1=[O:17].[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Br:18][C:15]1[C:8]2[C:7](=[O:17])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH2:12][CH2:11][CH2:10][C:9]=2[S:13][C:14]=1[CH3:16]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 19881100HCID 19881100, compound

Product 1

HCID 19881116HCID 19881116, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5.0 g of 5-(4-chlorobutyl)-5,6,7,8-tetrahydro-2-methyl-4H-thieno[3,2-c]azepin-4-one in 60 ml of acetic acid was added 1.9 ml of bromine at 60° C. and stirred for 20 minutes. After cooling, to the mixture was added an aqueous saturated sodium thiosulfate solution and the mixture was neutralized with potassium carbonate, and then extracted with ethyl acetate. The extract was washed with water, dried and concentrated under reduced pressure. The resulting crude crystals were recrystallized from a mixed solvent of isopropyl alcohol and hexane to give 2.3 g of 3-bromo-5-(4-chlorobutyl)-5,6,7,8-tetrahydro-2-methyl-4H-thieno[3,2-c]azepin-4-one as pale yellow crystals, melting at 78°-80° C.

Workup

  1. temperatureAfter cooling, to the mixture
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude crystals were recrystallized from a mixed solvent of isopropyl alcohol and hexane

Sources & evidence

ORD record
ord-55c99b8440024a61b28b26966a5f60ba
Source dataset
uspto-grants-1992_08
Patent number
US05141930

Reaction notes

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