Acetic Acid → 6-(2-Aminophenyl)-3-sulfanylidene-3,4-dihydro-1,2,4-triazin-5(2H)-one

HRID 2089266Notes

Reaction equation

HRID 2089266 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[NH2:12][NH:13][C:14]([NH2:16])=[S:15].C(O)(=O)C>[OH-].[K+]>[NH2:1][C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:4]1[C:2](=[O:3])[NH:16][C:14](=[S:15])[NH:13][N:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7054IsatinHCID 2723789Thiosemicarbazide

Product 1

HCID 7138866-(2-Aminophenyl)-3-sulfanylidene-3,4-dihydro-1,2,4-triazin-5(2H)-oneYield 86.2%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
115 °C

Procedure

This was prepared by a modified literature procedure (Doleschall, G.; Lempert, K. Tetrahedron 1973, 29, 639-649). Isatin (10 g, 67.96 mmol) was dissolved in ca. 10% aqueous KOH (9.9 g in 100 mL of water) and then treated with thiosemicarbazide (6.28 g; 68.90 mmol). After 1 hour of heating at 115° C. (bath temperature), the reaction mixture was poured over ice and treated with glacial acetic acid drop-wise, till the pH was ca. 5. The yellow fluffy precipitate was filtered, washed copiously with water (8×50 mL) and dried first in air and then under high vacuum to afford 12.9 g of yellow solid.

Workup

  1. customThis was prepared by a modified literature procedure (Doleschall, G.; Lempert, K. Tetrahedron 1973, 29, 639-649)
  2. additionthe reaction mixture was poured over ice
  3. filtrationThe yellow fluffy precipitate was filtered
  4. washwashed copiously with water (8×50 mL)
  5. customdried first in air

Sources & evidence

ORD record
ord-af0d249e9bf24cbb8dea2515d17a2a1a
Source dataset
uspto-grants-2013_05
Patent number
US08436031B2

Reaction notes

Loading…