Methanol → HCID 10224621, compound

HRID 1841592Notes

Reaction equation

HRID 1841592 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.CO.[CH3:34][N:35]([CH3:61])[CH2:36][CH2:37][CH2:38][CH2:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([NH:47][S:48]([C:51]2[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][CH:52]=2)(=[O:50])=[O:49])=[CH:43][CH:42]=1>C1COCC1>[CH3:61][N:35]([CH3:34])[CH2:36][CH2:37][CH2:38][CH2:39][O:40][C:41]1[CH:42]=[CH:43][C:44]([N:47]([CH3:1])[S:48]([C:51]2[CH:52]=[CH:53][C:54]([C:57]([F:59])([F:60])[F:58])=[CH:55][CH:56]=2)(=[O:50])=[O:49])=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11327500HCID 11327500, compound

Product 1

HCID 10224621HCID 10224621, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 98 mg (0.375 mmol) triphenylphosphine in 0.5 ml THF was treated at 0° C. with 0.06 ml (0.375 mmol) DEAD, then with 0.012 ml (0.3 mmol) methanol in 0.33 ml THF and finally with 104 mg (0.25 mmol) of N-[4-(4-Dimethylamino-butoxy)-phenyl]-4-trifluoromethyl-benzenesulfonamide in 0.3 ml THF. The reaction mixture was stirred over night at RT, evaporated and extracted with aqueous saturated NaHCO3/Et2O (3×). The organic phases were dried over Na2SO4 evaporated and purified by flash column chromatography on silica gel with CH2Cl2/MeOH (99:1 to 95:5) to yield 80 mg (74%) of N-[4-(4-Dimethylamino-butoxy)-phenyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, mp: 151-153° C.; MS: 431 (MH+).

Workup

  1. customevaporated
  2. extractionextracted with aqueous saturated NaHCO3/Et2O (3×)
  3. dry with materialThe organic phases were dried over Na2SO4
  4. customevaporated
  5. custompurified by flash column chromatography on silica gel with CH2Cl2/MeOH (99:1 to 95:5)

Sources & evidence

ORD record
ord-36dcd7170e514759b87c7f0684cd6085
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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