Stannous chloride dihydrate → HCID 21878463, compound

HRID 723961Notes

Reaction equation

HRID 723961 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl>C(O)C>[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 21878473HCID 21878473, compound

Product 1

HCID 21878463HCID 21878463, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2-morpholin-4-yl-ethyl)-(6-nitro-benzothiazol-2-yl)-amine (Example 26, 250 mg, 0.81 mmol) and tin(II) chloride dihydrate (914 mg, 5 eq.) in ethanol (30 mL) was heated at reflux for 6 hours. The reaction mixture was concentrated, treated with 1.0 N NaOH solution (50 mL), and extracted with ethyl acetate (2×100 mL). The organic layer was dried over MgSO4, concentrated and subjected to silica gel chromatography (10% 2M ammonia/methanol in CH2Cl2) to give the desired amine (175 mg, 77%). LCMS analysis (acetonitrile water, C18 silica) reveals 99.9% purity. MS (M+1, 279).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe reaction mixture was concentrated
  4. additiontreated with 1.0 N NaOH solution (50 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9af52d0c816a4c28a35e6dcc9ca6f35d
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

Loading…