HCID 20155817, compound → HCID 13361807, compound

HRID 2413500Notes

Reaction equation

HRID 2413500 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18]C)[CH:14]=3)[CH2:9]2)=[CH:4][CH:3]=1>C(O)(=O)C.Br>[OH:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:17][CH2:16]2

Participants

3

Reactant 1

HCID 20155817HCID 20155817, compound

Product 1

HCID 13361807HCID 13361807, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

7.0 g of the compound prepared under (b) are heated under reflux for 8 hours with a mixture of 50 ml of glacial acetic acid/hydrobromic acid (48% strength) in the volume ratio 1:1. After removing the acid in a rotary evaporator, the residue is taken up with methylene chloride/dilute ammonia, and the organic phase is dried and evaporated in a rotary evaporator. The oily residue is chromatographed on silica gel using a mixture of methylene chloride/ethyl acetate in the ratio 19:1. 2.2 g of pale yellow crystals (38% of theory) are obtained, melting point: 122°-123°.

Workup

  1. temperatureare heated
  2. customAfter removing the acid
  3. customin a rotary evaporator
  4. customthe organic phase is dried
  5. customevaporated in a rotary evaporator
  6. customThe oily residue is chromatographed on silica gel using
  7. additiona mixture of methylene chloride/ethyl acetate in the ratio 19:1

Sources & evidence

ORD record
ord-631915f2e3d74058a495f37f25ccd2ab
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

Loading…