Thionyl Chloride → HCID 18367388, compound

HRID 1741360Notes

Reaction equation

HRID 1741360 reaction equation
O[CH2:2][CH2:3][CH2:4][CH:5]([NH:23][CH:24]1[C:33]2[C:28](=[C:29]([O:34][CH3:35])[CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH2:25]1)[C:6]1[O:7][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1.O=S(Cl)Cl>C(Cl)Cl>[C:11]1([C:9]2[N:10]=[C:6]([CH:5]3[CH2:4][CH2:3][CH2:2][N:23]3[CH:24]3[C:33]4[C:28](=[C:29]([O:34][CH3:35])[CH:30]=[CH:31][CH:32]=4)[CH2:27][CH2:26][CH2:25]3)[O:7][C:8]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18367346HCID 18367346, compound

Product 1

HCID 18367388HCID 18367388, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[[4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butyl]amino]-5-methoxy-1,2,3,4-tetrahydronaphthalene (0.9 g) in CH2Cl2 (20 ml) was added SOCl2 (3 ml). After being stirred for 4 hours, the solvent was removed. The residue was dissolved in CH3CN (20 ml) and K2CO3 (5 g) was added to the solution. After being stirred for 4 hours under reflux, the solution was poured into the mixture of ethyl acetate and water. The organic layer was washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-[2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-methoxy-1,2,3,4-tetrahydronaphthalene (0.57 g). MS (m/z): 451 (M+ +1) IR (Neat): 1580 cm-1NMR (CDCl3, δ): 1.5-2.3 (8H, m), 2.4-3.2 (4H, m), 3.69 and 3.76 (3H, each s), 4.0-4.2 (2H, m), 6.4-6.72 (3H, m), 7.3-7.7 (10H, m)

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in CH3CN (20 ml)
  3. additionK2CO3 (5 g) was added to the solution
  4. stirringAfter being stirred for 4 hours
  5. temperatureunder reflux
  6. additionthe solution was poured into the mixture of ethyl acetate and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo
  10. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-247ef4999efe452ba43850071356d048
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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