Sodium Carbonate → 3-[[2-(4-Thiomorpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol

HRID 2396727Notes

Reaction equation

HRID 2396727 reaction equation
COC[O:4][C:5]1[CH:22]=[CH:21][C:8]2[C:9]([NH:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][S:18][CH2:17][CH2:16]3)=[N:10][O:11][C:7]=2[CH:6]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl>[N:15]1([CH2:14][CH2:13][NH:12][C:9]2[C:8]3[CH:21]=[CH:22][C:5]([OH:4])=[CH:6][C:7]=3[O:11][N:10]=2)[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 154351386-Methoxymethoxy-N-[2-(4-thiomorpholinyl)ethyl]-1,2-benzisoxazol-3-amine

Product 1

HCID 1358150603-[[2-(4-Thiomorpholinyl)ethyl]amino]-1,2-benzisoxazol-6-olYield 72.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6-Methoxymethoxy-N-[2-(4-thiomorpholinyl)ethyl]-1,2-benzisoxazol-3-amine (1.6 g Example 22) was dissolved in methanolic hydrochloric acid (40 ml) and stirred under nitrogen for 24 hours. The reaction was neutralized with saturated Na2CO3 solution, and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. The resulting residue was filtered through a silica gel filter-cake eluting with 5% MeOH/DCM, concentrated in vacuo, and subsequent titration with EtOAc provided the product (1.0 g).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. filtrationThe resulting residue was filtered through a silica gel
  5. filtrationfilter-cake
  6. washeluting with 5% MeOH/DCM
  7. concentrationconcentrated in vacuo, and subsequent titration with EtOAc

Sources & evidence

ORD record
ord-7eb032098fbb402fb950b22e7b2785d2
Source dataset
uspto-grants-1996_02
Patent number
US05494908

Reaction notes

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