Acetic Acid → HCID 178467481, compound

HRID 1722012Notes

Reaction equation

HRID 1722012 reaction equation
[C:1]([C:4]1[NH:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH3:17])(=[O:3])[CH3:2].C(O)(=O)C.Br.C([O-])(O)=O.[Na+]>O>[C:1]([C:4]1[NH:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH3:17])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 178488947HCID 178488947, compound

Product 1

HCID 178467481HCID 178467481, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 45 (1.0 g, 0.004 mol), glacial acetic acid (5.33 ml) and 48% HBr (22 ml) was heated at reflux for 3 hours with stirring. The reaction was cooled in an ice bath and the yellow precipitate was collected and combined with the residue resulting from concentration of the mother liquor. The solid was suspended in H2O (15 ml) and saturated NaHCO3 solution (41 ml) and stirred at ambient temperature overnight. The solids were collected, washed with H2O, and dried to yield 850 mg (98.4%) of 46; m.p. 300° C.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe reaction was cooled in an ice bath
  3. customthe yellow precipitate was collected
  4. customresulting from concentration of the mother liquor
  5. customThe solids were collected
  6. washwashed with H2O
  7. customdried

Sources & evidence

ORD record
ord-729ff33f09e54990bffc399d80cc5280
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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