Protocatechuic Acid → HCID 135856790, compound

HRID 1244771Notes

Reaction equation

HRID 1244771 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5](O)=O.[NH2:12][NH:13][C:14]([NH2:16])=[S:15].P(Cl)(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>O1CCOCC1>[CH:2]1([NH:16][C:14]2[S:15][C:5]([C:4]3[CH:3]=[C:2]([OH:1])[C:10]([OH:11])=[CH:9][CH:8]=3)=[N:12][N:13]=2)[CH2:3][CH2:4][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 72Protocatechuic AcidHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 2723789Thiosemicarbazide

Product 1

HCID 135856790HCID 135856790, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 3,4-dihydroxybenzoic acid (2.885 mmol, 0.445 g), thiosemicarbazide (5b) (2.885 mmol, 0.500 g) in anhydrous dioxane (10 mL) was added phosphorus oxychloride (3.751 mmol, 0.350 mL) at 90° C., and the mixture of sodium bicarbonate to pH 7 then stirred at RT overnight. The precipitate was filtered, washed with hexane, then dried to give the title compound. Yield: 71%.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with hexane
  3. customdried

Sources & evidence

ORD record
ord-3f1113323c944b86b02ce1114ce71b93
Source dataset
uspto-grants-2006_10
Patent number
US07122565B2

Reaction notes

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