P-Anisidine → HCID 19434098, compound

HRID 1736018Notes

Reaction equation

HRID 1736018 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11](Cl)(=[O:13])=[O:12].C1OC(C2C=CSC=2)OC1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1.C(N(CC)CC)C>C1COCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11]([NH:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 3156302-(3-Thienyl)-1,3-dioxolaneHCID 105389153-(1,3-dioxolan-2-yl)thiophene-2-sulfonyl Chloride

Product 1

HCID 19434098HCID 19434098, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(1,3-dioxolan-2-yl)-thiophene-2-sulfonyl chloride (11.16 g), prepared from thiophene-3-carboxaldehyde ethylene acetal as described in Example 6, Step A, in THF (100 mL) at 0° C. was combined with p-anisidine (7.87 g, 63.9 mmol) and triethylamine (4.04 g, 40 mmol). After stirring for 4 hr at ambient temperature, the mixture was evaporated to a residue which was extracted with ethyl acetate (2×150 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, 40% ethyl acetate/hexane) to give an oil (10.21 g, 75%).

Workup

  1. customthe mixture was evaporated to a residue which
  2. extractionwas extracted with ethyl acetate (2×150 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated to a residue which
  5. customwas purified by column chromatography (silica, 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-985edd1b453342fe82587fc02784107b
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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