Water → HCID 20145007, compound

HRID 1905992Notes

Reaction equation

HRID 1905992 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:13](=[O:16])[CH2:14][CH3:15])=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1.C(O)(=O)C.[BrH:21].Br.[NH+]1C=CC=CC=1.O>C(O)(=O)C>[CH3:1][NH:2][C:3]1[S:4][C:5]([C:13](=[O:16])[CH:14]([Br:21])[CH3:15])=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 20144987HCID 20144987, compoundHCID 21226041Pyridinium hydrobromideHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 20145007HCID 20145007, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl 2-methylamino-5-propionyl-4-thiazolecarboxylate (7.4 g) and 30% hydrogen bromide acetic acid (10 ml) in acetic acid (50 ml) was added pyridinium hydrobromide perbromide (13.0 g) at ambient temperature and the mixture was stirred for an hour. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to afford a crystalline residue, which was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give ethyl 2-methylamino-5-(2-bromopropionyl)-4-thiazolecarboxylate (7.4 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customto afford a crystalline residue, which
  6. customwas recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-0f8781f130c14b719fc84d577dc38529
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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