Thiourea → HCID 178425296, compound

HRID 1027483Notes

Reaction equation

HRID 1027483 reaction equation
C[O-].[Na+].[NH2:4][C:5]([NH2:7])=[S:6].C([O:10][C:11](=O)[CH:12]([NH:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1)[C:13](OCC)=[O:14])C>C(O)C>[OH:14][C:13]1[C:12]([NH:18][C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=2)=[C:11]([OH:10])[N:7]=[C:5]([SH:6])[N:4]=1

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 10942334Sodium MethoxideHCID 33240476Diethyl 2-(3-methylbenzamido)malonate

Product 1

HCID 178425296HCID 178425296, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

1.5 equivalents of sodium methoxide (30% in methanol) were added to 7.79 g of thiourea in 150 ml of absolute ethanol. A solution of 30 g of 2-(3-methyl-benzoylamino)malonic acid diethyl ester in 100 ml of absolute ethanol was added dropwise, and the reaction mixture was stirred at 60° C. for 2 h. Then the mixture was cooled to 0° C. for 30 min, and the precipitate was filtered off with suction, washed and dried. 28.6 g of the crude title compound were obtained.

Workup

  1. temperatureThen the mixture was cooled to 0° C. for 30 min
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-cb345fb32d0140bd88ee08a64e09f618
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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