Hydrochloric Acid → HCID 178434607, compound

HRID 1909057Notes

Reaction equation

HRID 1909057 reaction equation
CN(C)S([N:6]1[C:10]([CH2:11][CH2:12][CH2:13][Cl:14])=[C:9]([Br:15])[C:8]([CH3:16])=[N:7]1)(=O)=O.Cl>CO>[Br:15][C:9]1[C:8]([CH3:16])=[N:7][NH:6][C:10]=1[CH2:11][CH2:12][CH2:13][Cl:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 665996314-Bromo-5-(3-chloro-propyl)-3-methyl-pyrazole-1-sulfonic acid dimethylamide

Product 1

HCID 178434607HCID 178434607, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-5-(3-chloro-propyl)-3-methyl-pyrazole-1-sulfonic acid dimethylamide (3.85 g, 11.2 mmol) in MeOH (50 ml) at 0° C. was added 6 N HCl (50 mL). The reaction was warmed to room temperature and stirred overnight. The reaction was quenched by adding concentrated NH4OH until a pH of 8 was obtained. After concentrating to remove the MeOH, the remaining reaction solution was extracted with EtOAc and the organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified over normal phase silica starting with 10% EtOAc in heptane for 5 m and then increasing to 100% EtOAc over 40 m to give the desired product as a clear oil (2.42 g, 10.2 mmol). MS m/z 239.3 (M+H)+.

Workup

  1. customThe reaction was quenched
  2. additionby adding concentrated NH4OH until a pH of 8
  3. customwas obtained
  4. concentrationAfter concentrating
  5. customto remove the MeOH
  6. customthe remaining reaction solution
  7. extractionwas extracted with EtOAc
  8. dry with materialthe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was purified over normal phase silica starting with 10% EtOAc in heptane for 5 m
  12. temperatureincreasing to 100% EtOAc over 40 m

Sources & evidence

ORD record
ord-1bb0fc5b2d364c1688f48bae1f13d60a
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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