Water → HCID 10692234, compound

HRID 2292947Notes

Reaction equation

HRID 2292947 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.[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])#[N:16].O>CN(C)C(=O)C>[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[CH:28][CH:27]=1)(=[O:25])=[O:24])#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 10753680HCID 10753680, compound

Product 1

HCID 10692234HCID 10692234, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.82 g, 5.2 mmol) in N,N-dimethylacetamide (10 mL) was added thionyl chloride (0.62 g, 5.2 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 4-[(2-Cyanophenyl)sulfonyl]benzeneamine (1.00 g, 3.8 mmol) was added in one portion and the reaction mixture stirred at room temperature overnight. The mixture was poured into water and the aqueous solution decanted from an oily solid which was purified by flash column chromatography (5% v/v ethyl acetate/methylene chloride). Recrystallization from methylene chloride/hexane yielded the title propanamide as a white solid (1.08 g, 72%); mp 156°-158° C. 1H-NMR (250 MHz, d6-DMSO): 1.58 (s, 3H, CH3) 7.59 (s, 1H, OH) 7.88-8.13 (m, 7H, aromatic) 8.31 (d, 1H, J=6.9 Hz, aromatic) 10.50 (s, 1H, OH). MS (CI, CH4): 399 (M+1).

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. customthe aqueous solution decanted from an oily solid which
  3. customwas purified by flash column chromatography (5% v/v ethyl acetate/methylene chloride)
  4. customRecrystallization from methylene chloride/hexane

Sources & evidence

ORD record
ord-6ad3ccaad41e4d019de1be0b529d4466
Source dataset
uspto-grants-1997_11
Patent number
US05684198

Reaction notes

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