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

HRID 1003344Notes

Reaction equation

HRID 1003344 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-d7a249b2d860431c94aa6b822a24c6a7
Source dataset
uspto-grants-2000_04
Patent number
US06046203

Reaction notes

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