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Water → Methanesulfonic acid 3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl ester

HRID 221343
Notes
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Reaction equation

HRID 221343 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[C:15]([CH2:17][OH:18])[O:14][N:13]=2)=[CH:8][CH:7]=1.C(N(CC)CC)C.O>C(Cl)Cl>[N:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:16]=[C:15]([CH2:17][O:18][S:2]([CH3:1])(=[O:4])=[O:3])[O:14][N:13]=2)=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 37134678[3-(4-Pyridinyl)-1,2,4-oxadiazol-5-yl]methanol

Product 1

HCID 57954388Methanesulfonic acid 3-pyridin-4-yl-[1,2,4]oxadiazol-5-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Methanesulfonyl chloride (0.50 ml, 6.50 mmol) was added to a stirred solution of (3-pyridin-4-yl-[1,2,4]oxadiazol-5-yl)methanol (1 g, 5.65 mmol) and triethylamine (0.953 ml, 6.78 mmol) in CH2Cl2 (30 ml) at 0° C. After 10 min, water (20 ml) was added and the aqueous phase extracted with CH2Cl2 (20 ml). The combined organic phases were dried (MgSO4) and evaporated to afford the title compound: RT=2.32 min; m/z (ES+)=256.0 [M+H]+.

Workup

  1. extractionthe aqueous phase extracted with CH2Cl2 (20 ml)
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-d3ce24e9c3d44bf7bc856bcc84bcd56f
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08207147B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes