Phthalic Anhydride → 1-(2-Carboxybenzoyl)-2-methyl-4-phenyl-3-thiosemicarbazide

HRID 893876Notes

Reaction equation

HRID 893876 reaction equation
[CH3:1][N:2]([C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[S:5])[NH2:3].[C:13]1(=[O:23])[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>CN(C)C=O>[C:16]([C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[C:13]([NH:3][N:2]([CH3:1])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[S:5])=[O:23])([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 853583Sbb062267

Product 1

HCID 128811731-(2-Carboxybenzoyl)-2-methyl-4-phenyl-3-thiosemicarbazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methyl-4-phenyl-3-thiosemicarbazide (0.2 mole) was dissolved in about 75 ml of dimethylformamide and placed in a 3-necked round-bottomed flask equipped with magnetic stirrer, condenser, additional powder funnel and thermometer. Phthalic anhydride (0.2 mole) was added in portions at 20°. The contents were stirred overnight at room temperature, then poured into ice water the following morning. The resulting solid title product was recrystallized from a mixture of hexane and ethanol. (m.p. 155°-156°) yield, 70%.

Workup

  1. customplaced in a 3-necked round-bottomed flask
  2. customequipped with magnetic stirrer, condenser, additional powder funnel
  3. customThe resulting solid title product was recrystallized from a mixture of hexane and ethanol
  4. custom(m.p. 155°-156°) yield

Sources & evidence

ORD record
ord-a22f3431f21d42958dbb05a6faa6dcdc
Source dataset
uspto-grants-1981_08
Patent number
US04282031

Reaction notes

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