Hydrochloric Acid → HCID 18444043, compound

HRID 459670Notes

Reaction equation

HRID 459670 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=2)[N:5]=[CH:4][CH:3]=1.[ClH:16].[N:17](OCCC(C)C)=[O:18]>O1CCCC1>[ClH:16].[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[N:17]=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 17978868HCID 17978868, compound

Product 1

HCID 18444043HCID 18444043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

14.9 g (74 mmol) of 5-amino-1-(4-isopropylphenyl)pyrazole [sic] from Step 2.1 was dissolved in 130 mL of tetrahydrofuran. 42.2 g of 32% hydrochloric acid was added, and the reaction mixture was cooled to 0 to 5° C. Then, 9.5 g (81 mmol) of isopentyl nitrite was added dropwise with agitation so that the temperature did not exceed 5° C. Gradually, a yellowish precipitate formed which after an additional 1.5-hour agitation period in an ice bath was removed by suction filtration and washed with a small amount of tetrahydrofuran. Drying gave 12.3 g (46.1 mmol, 62% of the theoretical) of 5-amino-1-(4-isopropylphenyl)4-nitroso-1H-pyrazole hydrochloride.

Workup

  1. customdid not exceed 5° C
  2. customGradually, a yellowish precipitate formed which after an additional 1.5-hour agitation period in an ice bath
  3. customwas removed by suction filtration
  4. washwashed with a small amount of tetrahydrofuran
  5. customDrying

Sources & evidence

ORD record
ord-1584d05f46794db984e9e5220dcd7853
Source dataset
uspto-grants-2007_03
Patent number
US07195649B2

Reaction notes

Loading…