1,5-Diazabicyclo(4.3.0)non-5-ene → methyl 8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepin-11-carboxylate

HRID 1087560Notes

Reaction equation

HRID 1087560 reaction equation
Cl[CH:2]1[CH2:8][N:7]2[C:9](=[O:23])[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:6]2[C:5]2[S:24][CH:25]=[CH:26][C:4]=2[S:3]1.N12CCCC1=NCCC2>CS(C)=O>[O:23]=[C:9]1[N:7]2[CH:8]=[CH:2][S:3][C:4]3[CH:26]=[CH:25][S:24][C:5]=3[C:6]2=[C:12]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[C:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 14666701methyl 5-chloro-5,6-dihydro-8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepin-11-carboxylate

Product 1

HCID 14666703methyl 8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepin-11-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

ba) 6.05 g of methyl 5-chloro-5,6-dihydro-8 -oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepin-11-carboxylate were suspended in 60 ml of dimethyl sulfoxide. 3.6 ml of 1,5-diazabicyclo[4.3.0]non-5-ene were added, whereupon the mixture was heated to 70°-75° in order to complete the reaction. The mixture was then cooled to room temperature, whereby crystals separated. The mixture was poured into 300 ml of water, and the crystals were removed by filtration and washed with water. The still moist crystals were dissolved in chloroform. The solution was dried over sodium sulfate, filtered and evaporated in vacuo. After chromatography on silica gel, there was obtained methyl 8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepin-11-carboxylate as yellow crystals which were recrystallized from toluene. The product then has a m.p. of 207°-210°.

Workup

  1. temperaturewas heated to 70°-75° in order
  2. customthe reaction
  3. customwhereby crystals separated
  4. additionThe mixture was poured into 300 ml of water
  5. customthe crystals were removed by filtration
  6. washwashed with water
  7. dissolutionThe still moist crystals were dissolved in chloroform
  8. dry with materialThe solution was dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-3240625d4e224764b15b07fb43e43f1c
Source dataset
uspto-grants-1991_07
Patent number
US05036066

Reaction notes

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