Ethanol → HCID 70494741, compound

HRID 1981947Notes

Reaction equation

HRID 1981947 reaction equation
[BrH:1].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16]C(=O)C)[C:14](=[O:20])[N:13]([CH2:21][CH2:22][NH:23][CH3:24])[C:12]3[CH:25]=[CH:26][CH:27]=[CH:28][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].C(O)C>O>[BrH:1].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:20])[N:13]([CH2:21][CH2:22][NH:23][CH3:24])[C:12]3[CH:25]=[CH:26][CH:27]=[CH:28][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 70493723HCID 70493723, compound

Product 1

HCID 70494741HCID 70494741, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.8 g of (±)-cis-2-(4-methylphenyl)-3-acetoxy-5-[2-(N-methylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin- 4(5H)-one hydrobromide, 10 ml of 5% aqueous sodium hydroxide solution and 5 ml of ethanol is stirred at room temperature for 1 hours. After the reaction is completed, the mixture is diluted with water and the aqueous mixture is extracted with chloroform. The extract is washed with aqueous saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is converted to its hydrobromide and recrystallized from ethanol, whereby 0.58 g of (±)-cis-2-(4-methylphenyl)-3-hydroxy-5-[2-(N-methylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide is obtained as prisms.

Workup

  1. extractionthe aqueous mixture is extracted with chloroform
  2. washThe extract is washed with aqueous saturated sodium chloride solution
  3. customdried
  4. customevaporated
  5. customto remove solvent
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-74ac24a6d4584e8990eda5640133ba20
Source dataset
uspto-grants-1986_06
Patent number
US04594342

Reaction notes

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