hydroxylamine-O-sulfonic acid → HCID 11999273, compound

HRID 1364107Notes

Reaction equation

HRID 1364107 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:16][C:6]2[N:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:17])[CH2:3]1.[NH2:19]OS(O)(=O)=O>C(O)=O>[CH3:1][C:2]1([CH3:18])[CH2:3][C:4](=[O:17])[NH:19][C:5]2[S:9][C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[N:7][C:6]=2[CH2:16]1

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 6222625,5-DiMethyl-2-(Morpholin-4-yl)-5,6-dihydro-1,3-benzothiazol-7(4H)-one

Product 1

HCID 11999273HCID 11999273, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a stirred solution of Example 48 (1.00 g, 3.77 mmol) in formic acid (40 mL) was added, dropwise, hydroxylamine-O-sulfonic acid (0.64 g, 5.66 mmol). After refluxing overnight the reaction mixture was quenched with ice/water and neutralised with aqueous 5% NaOH and then extracted with DCM (2×40 μL). The organics were combined, dried (MgSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 3:1 DCM/EtOAc) gave the title compound (0.24 g, 22%) as an off-white solid. δH (DMSO-d6) 10.77 (1H, s), 3.69 (4H, m), 3.42 (4H, m), 2.52 (2H, s), 2.25 (2H, s), 0.98 (6H, s). LCMS (ES+) 282.0 (M+H)+.

Workup

  1. temperatureAfter refluxing overnight the reaction mixture
  2. customwas quenched with ice/water and neutralised with aqueous 5% NaOH
  3. extractionextracted with DCM (2×40 μL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 3:1 DCM/EtOAc)

Sources & evidence

ORD record
ord-9302409ac8bb4ff992894e04e22033f4
Source dataset
uspto-grants-2011_02
Patent number
US07888344B2

Reaction notes

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