Hydrochloric Acid → HCID 135979570, compound

HRID 1782164Notes

Reaction equation

HRID 1782164 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH:10][C:11](=O)[CH2:12][CH:13]([CH3:15])[CH3:14])[S:4][N:3]=1.Cl>N>[CH2:12]([C:11]1[NH:9][C:7](=[O:8])[C:6]2[C:2]([CH3:1])=[N:3][S:4][C:5]=2[N:10]=1)[CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54757315HCID 54757315, compound

Product 1

HCID 135979570HCID 135979570, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
140 °C

Procedure

The 3-methyl-5-(3-methyl-butyrylamino)-isothiazole-4-carboxylic acid amide (method 25) (45.8 g, 190 mmol) was suspended in 700 ml of 30% NH3 and then was heated to 140° C. for 5 h in a pressure reactor. The mixture was poured into a 4 L beaker and cooled in an ice bath. To the cold solution con HCl (560 ml) was added dropwise to pH 7.5 and a white precipitate was formed. The precipitated product was filtered off, washed with water (100 ml) and dried under vacuum overnight. 6-Isobutyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (11 g, 26%) was isolated as an off-white powder. 1H NMR (300 MHz) δ 1.05 (d, 6H), 2.32 (m, 1H), 2.69 (d, 2H), 2.82 (s, 3H).

Workup

  1. additionThe mixture was poured into a 4 L beaker
  2. temperaturecooled in an ice bath
  3. customa white precipitate was formed
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water (100 ml)
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-e1ca5c8115cc43c8aacefbb9bbb0407f
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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