Hydrogen Bromide → HCID 178516000, compound

HRID 746091Notes

Reaction equation

HRID 746091 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[NH:12][CH:13]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:5][CH:4]=1.Br>CC(O)=O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[NH:12][CH:13]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178490016HCID 178490016, compound

Product 1

HCID 178516000HCID 178516000, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of XIX (2.9 g, 0.01 mole), glacial HOAc (10 mL) and 48% HBr (35 mL) was stirred at reflux for 3 hours. The hot solution was decanted from the separated tar and chilled at 5°-10° C. overnight. The precipitated hydrobromide salt was collected, washed with Et2O, dissolved in H2O (100 mL), and the solution was made basic with saturated NaHCO3 solution. The solid was collected, chromatographed on silica gel, and the product eluted with 95CHCl3 --5CH3OH--0.5H2O to yield 0.725 g (27%) of XX; m.p. 165.5°-167° C. (50% CH3OH).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe hot solution was decanted from the separated tar
  3. temperaturechilled at 5°-10° C. overnight
  4. customThe precipitated hydrobromide salt was collected
  5. washwashed with Et2O
  6. dissolutiondissolved in H2O (100 mL)
  7. customThe solid was collected
  8. customchromatographed on silica gel
  9. washthe product eluted with 95CHCl3 --5CH3OH--0.5H2O

Sources & evidence

ORD record
ord-a24206cf145840408f5321f0156b6ec3
Source dataset
uspto-grants-1986_07
Patent number
US04602093

Reaction notes

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