Hydrochloric Acid → HCID 57752427, compound

HRID 225417Notes

Reaction equation

HRID 225417 reaction equation
Cl.[OH:2][NH2:3].[OH-].[K+].[Cl:6][C:7]1[C:11]([C:12](Cl)=[O:13])=[C:10]([Cl:15])[N:9]([CH3:16])[N:8]=1.Cl>O.O1CCCC1>[Cl:6][C:7]1[C:11]([C:12]([NH:3][OH:2])=[O:13])=[C:10]([Cl:15])[N:9]([CH3:16])[N:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 221694993,5-Dichloro-1-methylpyrazole-4-carbonyl chloride

Product 1

HCID 57752427HCID 57752427, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a solution of hydroxyamine hydrochloride (106.9 g, 1.538 mol) in water (200 ml), a solution of 85% potassium hydroxide (101.5 g, 1.538 mol) in water (200 ml) was added at 5 to 15° C., and stirred at room temperature for 5 minutes. Then, a solution of 3,5-dichloro-1-methylpyrazole-4-carboxylic acid chloride (100.0 g, 0.5128 mol) in tetrahydrofuran (170 ml) was added dropwise at 3 to 8° C. over 2 hours. After stirring at 5° C. for 0.5 hour, the mixture was adjusted to pH 3-4 by adding 35% hydrochloric acid. Precipitated solid was filtered off, washed with water, and dried to obtain the aimed product (94.9 g). Melting point 200-202° C. (decomposition). Proton nuclear magnetic resonance chemical shift values δ (ppm) (in dimethylsulfoxide-d6) 3.79 (s, 3H), 9.24 (brs, 1H), 10.83 (brs, 1H).

Workup

  1. stirringAfter stirring at 5° C. for 0.5 hour
  2. customPrecipitated solid
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8ec228493d374d539b451ac85952a42d
Source dataset
uspto-grants-2009_07
Patent number
US07557067B2

Reaction notes

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