Water → HCID 19864286, compound

HRID 1199926Notes

Reaction equation

HRID 1199926 reaction equation
B(F)(F)F.[CH3:5][CH2:6][O:7]CC.[CH3:10][N:11]1[CH2:17][CH2:16][C:15]2[CH:18]=[CH:19][S:20][C:14]=2[CH:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:12]1.O.[OH-].[Na+].[Cl:30]CCl>C(OC(=O)C)(=O)C.C(O)C>[ClH:30].[C:6]([C:19]1[S:20][C:14]2[CH:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:12][N:11]([CH3:10])[CH2:17][CH2:16][C:15]=2[CH:18]=1)(=[O:7])[CH3:5]

Participants

8

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 19864284HCID 19864284, compound

Product 1

HCID 19864286HCID 19864286, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Boron trifluoride etherate (0.69 ml) was added dropwise to a stirred solution of 6-methyl-8-phenyl-5,6,7,8-tetrahydro-4H-thieno[2,3-d]azepine (0.46 g) in acetic anhydride (5 ml) at room temperature. After 16 hours, water (30 ml) and dichloromethane (30 ml) were added and the stirred mixture basified to pH~10 with 2M sodium hydroxide. This was extracted with dichloromethane (2×30 ml) and the extracts were dried, filtered and evaporated to a brown oil. Chromatography on silica eluting with 2% methanol in dichloromethane gave a yellow oil. This was dissolved in ethanol and ethanolic hydrogen chloride, evaporated and the title product recrystallised from ethanoldiethylethyl (m.p. 170°-176° C.).

Workup

  1. extractionThis was extracted with dichloromethane (2×30 ml)
  2. customthe extracts were dried
  3. filtrationfiltered
  4. customevaporated to a brown oil
  5. customChromatography on silica eluting with 2% methanol in dichloromethane gave a yellow oil
  6. customethanolic hydrogen chloride, evaporated
  7. customthe title product recrystallised from ethanoldiethylethyl (m.p. 170°-176° C.)

Sources & evidence

ORD record
ord-9a9bb14bda75486da177e23fbbd53a47
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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