Acetic Acid → HCID 131710702, compound

HRID 328158Notes

Reaction equation

HRID 328158 reaction equation
C([CH2:8][NH:9][CH2:10][CH2:11][C:12]1([C:25]([O:27][CH3:28])=[O:26])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[CH2:15][CH2:14][C:13]1=[O:24])C1C=CC=CC=1.Br.C(O)(=O)C.BrBr.[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>>[CH2:8]([N:9]1[CH2:10][CH2:11][C:12]2([C:25]([O:27][CH3:28])=[O:26])[C:13](=[O:24])[CH:14]1[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][C:21]=12)[C:38]1[CH:37]=[CH:36][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 5

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 8058Hexane2×HCID 24408BromineHCID 86734601HCID 86734601, compound

Product 1

HCID 131710702HCID 131710702, compound

Procedure

A solution of IV hydrobromide (0.13 m.) in 350 ml. acetic acid was treated dropwise with a solution of bromine (0.13 m) in 50 ml. acetic acid. After stirring for 1/2 hour, the reaction was diluted with 1.5 1. "Skellysolve B" (essentially n-hexane) and cooled. The precipitated residue was separated by decantation and washed with cold "Skellysolve B". The residue was taken up in methylene chloride and treated with dilute ammonium hydroxide until basic. The layers were separated and the aqueous layer extracted two times more with methylene chloride. The combined extracts were dried (MgSO4) and concentrated. The residue was taken up in acetone and allowed to crystallize with stirring. The crystals were collected to give V (69%). The analytical sample was recrystallized from methanol; mp 158°-160° C.

Workup

  1. additionthe reaction was diluted with 1.5 1
  2. customThe precipitated residue was separated by decantation
  3. washwashed with cold "Skellysolve B"
  4. additiontreated with dilute ammonium hydroxide until basic
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted two times more with methylene chloride
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. concentrationconcentrated
  9. customto crystallize
  10. stirringwith stirring
  11. customThe crystals were collected
  12. customto give V (69%)
  13. customThe analytical sample was recrystallized from methanol

Sources & evidence

ORD record
ord-997d32dee7cf4f67b7aeba9f6a2d3d18
Source dataset
uspto-grants-1977_04
Patent number
US04016167

Reaction notes

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