Potassium Carbonate → HCID 67263356, compound

HRID 1040616Notes

Reaction equation

HRID 1040616 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N+:6]([C:9]1[CH:10]=[C:11]2[C:17](=[CH:18][CH:19]=1)[CH:16]1[O:20][CH:12]2[CH2:13][NH:14][CH2:15]1)([O-:8])=[O:7].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:1][S:2]([N:14]1[CH2:13][CH:12]2[O:20][CH:16]([C:17]3[C:11]2=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:19][CH:18]=3)[CH2:15]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 67264550HCID 67264550, compound

Product 1

HCID 67263356HCID 67263356, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Methanesulfonyl chloride (133 mg, 1.16 mmol) was added to a solution of 4-nitro-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (200 mg, 0.55 mmol) and potassium carbonate (276 mg, 2.0 mmol) in THF (5 mL). The solution was stirred at 70° C. for 1 h. The reaction was then concentrated and purified with silica gel chromatography (0-100% EtOAc in hexanes) to give 10-Methanesulfonyl-4-nitro-12-oxa-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene as a light tan solid (150 mg, 54%). MS (m/e) 285 (M+1).

Workup

  1. concentrationThe reaction was then concentrated
  2. custompurified with silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4a63fe312c6b4cf9be378d184689f7e7
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…