p-Toluenesulfonic acid → HCID 67152210, compound

HRID 600686Notes

Reaction equation

HRID 600686 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=1)[C:5]#[N:6].[CH2:18](OC(OCC)OCC)C.CC1C=CC(S(O)(=O)=O)=CC=1>C1COCC1.C(Cl)Cl>[Br:17][C:13]1[CH:12]=[C:11]([N:10]2[C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[N:1]=[CH:18]2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 43518115HCID 43518115, compound

Product 1

HCID 67152210HCID 67152210, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of compound D (1 g, 3.47 mmol), triethylorthoformate (660 mg, 4.5 mmol) and PTSA (200 mg, 1.16 mmol) in THF (10 mL) was stirred at 70° C. for 4 h. After cooling to RT, the reaction mixture was diluted with DCM, washed with sat. NaHCO3 solution to remove PTSA, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography using 40% ethylacetate in hexane to afford compound 4 (1 g, 96%) as light brown solid, mp:168.5-174.4° C.

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with sat. NaHCO3 solution
  3. customto remove PTSA
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fdd2f4258ed64264b854660cfa5ffc2a
Source dataset
uspto-grants-2011_03
Patent number
US07902230B2

Reaction notes

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