Dimethyl acetylsuccinate → HCID 686779, compound

HRID 1399556Notes

Reaction equation

HRID 1399556 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]([CH:8]([CH2:13][C:14]([O:16]C)=[O:15])[C:9](OC)=[O:10])(=O)[CH3:6].C[O-].[Na+]>CO>[CH3:6][C:5]1[NH:4][C:2](=[S:3])[NH:1][C:9](=[O:10])[C:8]=1[CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 112039Dimethyl acetylsuccinateHCID 2723790ThioureaHCID 10942334Sodium Methoxide

Product 1

HCID 686779HCID 686779, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiourea (4.00 g; 52.5 mmol) and dimethyl acetylsuccinate (9.41 g; 50 mmol) were added at room temperature to a solution of sodium methoxide (22.87 ml; 100 mmol) in methanol (18 ml) and the mixture is stirred under reflux for 18 h. After cooling, the precipitate was filtered off and added with stirring to a hydrochloric acid solution (12N) at 0° C. The white precipitate was filtered, washed with water and dried under reduced pressure over phosphorus pentoxide to give 7.3 g (73%) of title compound as a white powder.

Workup

  1. temperatureunder reflux for 18 h
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. additionadded
  5. stirringwith stirring to a hydrochloric acid solution (12N) at 0° C
  6. filtrationThe white precipitate was filtered
  7. washwashed with water
  8. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-a3942ed5f65040c483bf2c33cdf27cb8
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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