HCID 23669492, compound → Sulfuric Acid

HRID 1658454Notes

Reaction equation

HRID 1658454 reaction equation
[OH2:1].C[O:3][C:4]1C=CC(N([S:12]([O-:15])(=[O:14])=[O:13])N)=C[CH:5]=1.[Na+].ClC1S[CH:20]=[C:21]([C:23](Cl)=[O:24])N=1>O.C(O)(C)(C)C>[C:23]([OH:24])(=[O:1])[CH2:21][CH2:20][C:4]([CH3:5])=[O:3].[S:12](=[O:13])(=[O:24])([OH:14])[OH:15]

Participants

6

Reactant 2

HCID 23669492HCID 23669492, compoundHCID 450815362-Chloro-1,3-thiazole-4-carbonyl chloride

Product 2

HCID 1118Sulfuric AcidHCID 11579Levulinic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

25.8 g (0.1 mole) of sodium p-methoxyphenylhydrazine sulphonate monohydrate are dissolved in a mixture of 112 ml of water and 48 ml of tert. butanol, and 20 g (0.11 mole) of 2-chlorothiazole-4-carboxylic acid chloride added. The reaction mixture is stirred at room temperature for an hour and at 70°C for another hour. Then, without isolating the product, 43.5 ml of levulinic acid and 5 ml of concentrated sulphuric acid are added, and the mixture is stirred at 80°C for 4 hours. On diluting the reaction mixture with water, the precipitated product is filtered by suction and recrystallized from tert. butanol, affording 23 g of 1-(2-chlorothiazole-4-yl-carboxylic)-2-methyl-5-methoxy-indole-3-yl acetic acid. Yield: 65%, m.p. 158°-160°C.

Workup

  1. additionadded

Sources & evidence

ORD record
ord-2297db75ef264eeb840b4ba1b4dd4fea
Source dataset
uspto-grants-1976_06
Patent number
US03964894

Reaction notes

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