Triethylamine → 1-Methyl-1H-pyrazole-4-sulfonic acid (2,2-dimethoxy-ethyl)-methyl-amide

HRID 553499Notes

Reaction equation

HRID 553499 reaction equation
[CH3:1][O:2][CH:3]([O:7][CH3:8])[CH2:4][NH:5][CH3:6].C(N(CC)CC)C.[CH3:16][N:17]1[CH:21]=[C:20]([S:22](Cl)(=[O:24])=[O:23])[CH:19]=[N:18]1>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:7][CH3:8])[CH2:4][N:5]([CH3:6])[S:22]([C:20]1[CH:19]=[N:18][N:17]([CH3:16])[CH:21]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85032,2-DimethoxyethylmethylamineHCID 170247301-methyl-1H-pyrazole-4-sulfonyl chloride

Product 1

HCID 673674041-Methyl-1H-pyrazole-4-sulfonic acid (2,2-dimethoxy-ethyl)-methyl-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cool a solution of methylaminoacetaldehyde dimethyl acetal (22.5 mL, 0.18 mol) and triethylamine (26.5 mL, 0.19 mol) to 0° C. in CH2Cl2, then add dropwise a solution of 1-methyl-1H-pyrazole-4-sulfonyl chloride (30 g, 0.17 mol). Stir the reaction mixture at room temperature overnight, dilute with CH2Cl2 (500 mL), and wash with water. Dry the combined organics over Na2SO4, filter and concentrate. The resulting oil is placed under high vacuum and within two hours a resulting off white solid is formed, which is used without further purification (38.22 g, 87%).

Workup

  1. washwash with water
  2. dry with materialDry the combined organics over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. waitThe resulting oil is placed under high vacuum and within two hours
  6. customa resulting off white solid is formed
  7. customwhich is used without further purification (38.22 g, 87%)

Sources & evidence

ORD record
ord-d2543f19f53948808fec9e1c51aa7f39
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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