Dipropylamine → N-[4-(N,N-Dipropylaminosulfonyl)phenyl]-3,3,3-trifluro-2-hydroxy-2-methylpropanamide

HRID 1938169Notes

Reaction equation

HRID 1938169 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([OH:18])([CH3:17])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](F)(=[O:15])=[O:14])=[CH:9][CH:8]=1)=[O:5].[CH2:21]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:22][CH3:23]>CN(C)C1C=CN=CC=1.C(#N)C.O>[CH2:21]([N:24]([CH2:25][CH2:26][CH3:27])[S:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4](=[O:5])[C:3]([OH:18])([CH3:17])[C:2]([F:20])([F:19])[F:1])=[CH:8][CH:9]=1)(=[O:15])=[O:14])[CH2:22][CH3:23]

Participants

6

Reactant 2

HCID 8902DipropylamineHCID 105914083,3,3-trifluoro-N-(4-flurosulfonylphenyl)-2-hydroxy-2-methylpropanamide

Product 1

HCID 9800873N-[4-(N,N-Dipropylaminosulfonyl)phenyl]-3,3,3-trifluro-2-hydroxy-2-methylpropanamideYield 34.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
22 °C

Procedure

A solution of 3,3,3-trifluoro-N-[4-(fluorosulfonyl)phenyl]-2-hydroxy-2-methylpropanamide (0.2 g), di-n-propylamine (0.25 g), and 4-dimethylaminopyridine (13.0 mg) in dry acetonitrile (3 ml) was heated at reflux for 4 days. The reaction mixture was cooled to 22° C., diluted with water (30 ml) and extracted with ethyl acetate (2×15 ml). The combined ethyl acetate extracts were washed with 1N HCl, brine, dried and evaporated to give an oil. The oil was purified by chromatography (12:1 CHCl3 : diethyl ether) to yield an oil which crystallized from hexane to produce the title compound as a colourless crystalline solid (87.5 mg); mp 132°-134° C.; MS: m/z=397(M+1); NMR (250M Hz): 0.77-0.83 (t,6), 1.41-1.49 (m,4), 1.58 (s,3), 2.96-3.02 (t,4), 7.54 (s,1), 7.72-7.75 (m,2), 7.96-7.98 (m,2), 10.36 (s,1). Analysis for C16H23 F3N2O4S: Calculated: C, 48.47; H, 5.85; N, 7.07; Found: C, 48.84; H, 5.90; N, 6.89.

Workup

  1. temperatureat reflux for 4 days
  2. extractionextracted with ethyl acetate (2×15 ml)
  3. washThe combined ethyl acetate extracts were washed with 1N HCl, brine
  4. customdried
  5. customevaporated
  6. customto give an oil
  7. customThe oil was purified by chromatography (12:1 CHCl3 : diethyl ether)
  8. customto yield an oil which
  9. customcrystallized from hexane

Sources & evidence

ORD record
ord-84c65df045854520b381b14af2f1d10c
Source dataset
uspto-grants-1997_12
Patent number
US05693639

Reaction notes

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