Water → HCID 21695287, compound

HRID 847386Notes

Reaction equation

HRID 847386 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][S:16][C:10]=2[S:9][CH2:8][CH2:7]1.[Br:17]Br.O>C(O)(=O)C>[Br:17][C:15]1[S:16][C:10]2[S:9][CH2:8][CH2:7][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[C:12](=[O:13])[C:11]=2[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 19881109HCID 19881109, compound

Product 1

HCID 21695287HCID 21695287, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3.0 g of 4-(4-chlorobutyl)-2,3-dihydrothieno[3,2-f]-1,4-thiazepin-5(4H)-one in 60 ml of acetic acid was added 1.5 ml of bromine with stirring at 60° C. and the mixture was stirred for 20 minutes at the same temperature. The mixture was poured into chilled water and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and the solvent was distilled off. The resulting crystals were recrystallized from ethanol to give 2.0 g of 7-bromo-4-(4-chlorobutyl)-2,3-dihydrothieno[3,2-f]-1,4-thiazepin-5(4H)-one as white crystals, melting at 81°-89° C.

Workup

  1. stirringthe mixture was stirred for 20 minutes at the same temperature
  2. additionThe mixture was poured
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-38454bc0a8d9466b9793d89b252eeb93
Source dataset
uspto-grants-1992_08
Patent number
US05141930

Reaction notes

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