1,2-Dimethoxyethane → 1-(2-Carboxybenzoyl)-2-methyl-4-phenyl-3-thiosemicarbazide, ammonium salt

HRID 893877Notes

Reaction equation

HRID 893877 reaction equation
[C:1]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([NH:8][N:9]([CH3:19])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[S:11])=[O:7])([OH:3])=[O:2].C(COC)OC.[NH4+].[OH-]>C(O)C>[NH4+:8].[C:1]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([NH:8][N:9]([CH3:19])[C:10]([NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[S:11])=[O:7])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 14923Ammonium HydroxideHCID 128811731-(2-Carboxybenzoyl)-2-methyl-4-phenyl-3-thiosemicarbazide

Product 1

HCID 1317123061-(2-Carboxybenzoyl)-2-methyl-4-phenyl-3-thiosemicarbazide, ammonium salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The free acid compound of Example 4 was suspended in 100 ml of ethanol and placed in a 300 ml round-bottomed flask equipped with magnetic stirrer and condenser. Twenty ml of dimethoxyethane were added to make the compound go into solution. After most of the solid had gone into solution, NH4OH was added. There was no discernible heat evolution. Solvents were evaporated. The resulting solid (title product) was refluxed in a mixture of hexane and ethanol and was then recovered by filtration. Yield 4.3 g. (m.p. 165°-166°).

Workup

  1. customplaced in a 300 ml round-bottomed flask
  2. customequipped with magnetic stirrer and condenser
  3. additionwas added
  4. customSolvents were evaporated
  5. temperatureThe resulting solid (title product) was refluxed in a mixture of hexane and ethanol
  6. filtrationwas then recovered by filtration

Sources & evidence

ORD record
ord-45d34ce13f6b44bcb98e13f2464214a4
Source dataset
uspto-grants-1981_08
Patent number
US04282031

Reaction notes

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