Triethylamine → HCID 86671738, compound

HRID 595004Notes

Reaction equation

HRID 595004 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][C:10]2([CH2:14][OH:15])[CH2:13][O:12][CH2:11]2)[CH:8]=1)([O-:3])=[O:2].C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>C(Cl)Cl>[CH3:26][S:23]([O:15][CH2:14][C:10]1([CH2:9][N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6]2)[CH2:13][O:12][CH2:11]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66765542HCID 66765542, compound

Product 1

HCID 86671738HCID 86671738, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(3-((4-nitro-1H-pyrazol-1-yl)methyl)oxetan-3-yl)methanol (0.6 g, 2.8 mmol) was dissolved in DCM (16 ml) with triethylamine (0.778 mL, 5.6 mmol) and the reaction was cooled at 0° C. Mesyl chloride (0.415 g, 3.62 mmol) was added dropwise and the reaction was allowed to reach rt overnight. The mixture was diluted in DCM (25 mL), washed with water (20 mL) and the water re-extracted with DCM (20 mL). The combined organics were dried over Na2SO4, filtered and the solvent removed under vacuum. (3-((4-nitro-1H-pyrazol-1-yl)methyl)oxetan-3-yl)methyl methanesulfonate was obtained as a yellowish oil (0.9 g, quantitative yield).

Workup

  1. washwashed with water (20 mL)
  2. extractionthe water re-extracted with DCM (20 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-939274dabc884160b9627c83cf894a60
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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