Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 4695-19-6

HRID 2296347Notes

Reaction equation

HRID 2296347 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[C:6]([CH3:13])([CH3:12])[C:7](OCC)=[O:8]>C(O)C>[CH3:12][C:6]1([CH3:13])[S:3][C:2](=[NH:4])[NH:1][C:7]1=[O:8]

Participants

4

Reactant 2

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 2723790Thiourea2×

Product 1

HCID 1377015474695-19-6

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of thiourea (19.0 g, 0.25 mole) in 150 ml of ethanol was heated under reflux until all of the thiourea had dissolved. Ethyl 2-bromo-isobutyrate (49.0 g, 0.25 mole) was then added over 10 minutes to the refluxing solution, after which time the solution was heated under reflux for six hours then allowed to stir at ambient temperature 36 hours. The solution was concentrated to dryness and the residue treated with water, then with aqueous NaHCO3 to adjust the pH to 7.0. The precipitated solid was collected by filtration, washed with water and dried to yield 5,5-dimethyl-2-iminothiazolidin-4-one: mp 252°-254° C.; 15.0 g (0.12 mole, 47%). Structure was confirmed by IR and NMR.

Workup

  1. temperaturewas heated
  2. dissolutionhad dissolved
  3. temperatureafter which time the solution was heated
  4. temperatureunder reflux for six hours
  5. concentrationThe solution was concentrated to dryness
  6. additionthe residue treated with water
  7. filtrationThe precipitated solid was collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-b8f0a2bc7c98474694d91484736c19de
Source dataset
uspto-grants-1984_01
Patent number
US04428948

Reaction notes

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