Sulfuric Acid → HCID 13377186, compound

HRID 1903563Notes

Reaction equation

C(O[C:5](=[O:7])[CH3:6])(=O)C.C(C#N)(=O)[C:9]([CH3:12])([CH3:11])[CH3:10].S(=O)(=O)(O)O.[CH3:21][NH:22][C:23](=[S:26])[NH:24][NH2:25].[OH-].[Na+]>Cl>[C:9]([CH:6]1[NH:25][NH:24][C:23](=[S:26])[N:22]([CH3:21])[C:5]1=[O:7])([CH3:10])([CH3:11])[CH3:12]

Participants

Conditions

Temperature: 40 °C

Procedure

First 51.2 g (0.5 mol) of acetic acid anhydride and then 27.8 g (0.25 mol) of pivaloyl cyanide were introduced, in each case at room temperature, into 98.0 g (1.0 mol) of initially introduced concentrated sulphuric acid. After this reaction mixture has been stirred for a further hour at 40° C., it was stirred into a solution of 23.3 g (0.25 mol) of 4-methyl-thiosemicarbazide in 200 ml of 1 N HCl. After the end of the addition, the mixture was stirred for a further hour at room temperature. The pH value was then adjusted to about 5 with 1,200 ml of 2 N NaOH, and the mixture was warmed to 80° C. for one hour. After the mixture had cooled, the precipitated reaction product was filtered off under suction, washed with 200 ml of water and dried. 45.8 g (92% of theory) of 6-tert.-butyl-4-methyl-5-oxo-3-thioxo-tetrahydro-1,2,4-(2H, 4H)-triazine were obtained as colorless crystals of melting point 214° C.; purity according to gas chromatographic determination >99%. For subsequent reactions, no further purification operations were required.

Workup

additionAfter the end of the addition
stirringthe mixture was stirred for a further hour at room temperature
temperaturethe mixture was warmed to 80° C. for one hour
temperatureAfter the mixture had cooled
customthe precipitated reaction product
filtrationwas filtered off under suction
washwashed with 200 ml of water
customdried

Sources & evidence

ORD record: ord-e68dd496ad2c4e3d9641dc561f853a07
Source dataset: uspto-grants-1984_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04436905

Reaction notes

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