Dimethyl Sulfoxide → HCID 14461329, compound

HRID 1073098Notes

Reaction equation

HRID 1073098 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.CS(C)=O.[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:26]([CH2:39][OH:40])=[C:27]([CH:36]([CH3:38])[CH3:37])[O:28][C:29]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:21][C:20]=1[O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(N(CC)CC)C>ClCCl>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:26]([CH:39]=[O:40])=[C:27]([CH:36]([CH3:38])[CH3:37])[O:28][C:29]=2[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:21][C:20]=1[O:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 14461328HCID 14461328, compound

Product 1

HCID 14461329HCID 14461329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 13.8 ml (97 mmol) of trifluoroacetic anhydride in 90 ml of dichloromethane is added dropwise at -70° C. to -65° C. to 9.2 ml (130 mmol) of dimethyl sulphoxide in 70 ml of anhydrous dichloromethane and the mixture is stirred at this temperature for 10 minutes. 26.1 g (665 mmol) of the compound from Example 24, dissolved in 500 ml of dichloromethane, are then added dropwise and the mixture is stirred for 1 more hour at -65° C. 26.9 ml (195 mmol) of triethylamine are now added and the mixture is held at the same temperature for a further 10 minutes. After warming to RT, the mixture is washed with saturated bicarbonate solution and sodium chloride solution and dried over sodium sulphate, and the solvent is removed in vacuo. After boiling the residue with ethanol, 17.6 g (68%) of colorless solid remain of m.p.: 137° C. By cooling the ethanolic solution, a further 5.6 g (21%) are produced of m.p.:138° C.

Workup

  1. additionare then added dropwise
  2. stirringthe mixture is stirred for 1 more hour at -65° C
  3. waitthe mixture is held at the same temperature for a further 10 minutes
  4. washthe mixture is washed with saturated bicarbonate solution and sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is removed in vacuo
  7. temperatureBy cooling the ethanolic solution
  8. customa further 5.6 g (21%) are produced of m.p.:138° C.

Sources & evidence

ORD record
ord-91dbebe55dee4afda5a52c99fb4b951f
Source dataset
uspto-grants-1990_11
Patent number
US04968681

Reaction notes

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