Water → HCID 10833567, compound

HRID 327168Notes

Reaction equation

HRID 327168 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20]([C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21].O>CN(C)C(=O)C>[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[S:20]([C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[CH:25][CH:24]=1)(=[O:21])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 21480143HCID 21480143, compound

Product 1

HCID 10833567HCID 10833567, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.50 g, 3.1 mmol) in N,N-dimethylacetamide (7 mL) was added thionyl chloride (0.37 g, 3.1 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 4-(2-Thienylsulfonyl)benzenamine (0.50 g, 2.1 mmol) was added in one portion to the orange solution and the mixture stirred at room temperature overnight. The brown solution was poured into water and the aqueous solution extracted with ethyl acetate (2×50 mL). The organics were combined, dried (MgSO4), filtered and the solvent distilled to yield a tan solid. Flash chromatography of the solid (eluted with 5% v/v ethyl acetate in methylene chloride) and evaporation of the eluent yielded the title propanamide (0.61 g, 77%) as an off-white solid; mp 158°-161 0C. 1H--NMR (250 MHz, d6 --DMSO): 1.57 (s, 3H, CH3), 7.21 (dd, 1H, J=4.9, 4.0 Hz, aromatic), 7.56 (s, 1H, OH), 7.81 (dd, 1H, J=3.8, 1.5 Hz, aromatic), 8.00 (m, 5H, aromatic), 10.43 (s, 1H, NH). MS (CI, CH4): 380(M+1).

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. extractionthe aqueous solution extracted with ethyl acetate (2×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. distillationthe solvent distilled
  6. customto yield a tan solid
  7. washFlash chromatography of the solid (eluted with 5% v/v ethyl acetate in methylene chloride) and
  8. customevaporation of the eluent

Sources & evidence

ORD record
ord-11ab1aab0fc44a819f5f530480c2a634
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

Loading…