Methanol → HCID 178499525, compound

HRID 749159Notes

Reaction equation

HRID 749159 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][C:8]([OH:10])=[O:9])[CH:3]=1.S(Cl)(Cl)=O.[CH3:15]O>>[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][C:8]([O:10][CH3:15])=[O:9])[CH:3]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 178507647HCID 178507647, compound

Product 1

HCID 178499525HCID 178499525, compoundYield 48%

Procedure

(5-amino-1H-pyrazol-3-yl)acetic acid (3.02 g, 0.022 mmol) in methanol (32 ml) was added to a mixture of methanol (32 ml) and thionyl chloride (3.15 ml) at 0° C. The resulting mixture was stirred for 18 hours, evaporated and the residue purified by chromatography on silica gel, eluting with methanol:ammonia:dichloromethane (9:1:90), to yield methyl (5-amino-1H-pyrazol-3-yl)acetate (1.58 g, 48% yield):

Workup

  1. customevaporated
  2. customthe residue purified by chromatography on silica gel
  3. washeluting with methanol:ammonia:dichloromethane (9:1:90)

Sources & evidence

ORD record
ord-b91c6c38422144f5b80c5569dc2a4c9e
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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