Hydrochloric Acid → HCID 131735648, compound

HRID 530643Notes

Reaction equation

HRID 530643 reaction equation
[O:1]=[S:2]1(=[O:15])[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]([OH:14])[C:10]([F:13])([F:12])[F:11])[CH2:4][CH2:3]1.C(#N)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1.Cl>CCOCC.CCCCCC>[ClH:19].[O:15]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([CH2:8][C@H:9]([O:14][C:27](=[O:28])[NH:26][C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)[C:10]([F:13])([F:11])[F:12])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 76934-Chlorophenyl IsocyanateHCID 118276755HCID 118276755, compound

Product 1

HCID 131735648HCID 131735648, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

In a 10 mL round-bottomed flask, (S)-3-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-1,1,1-trifluoro-propan-2-ol (120 mg, 485 μmol) was combined with acetonitrile (5.00 ml) to give a colorless solution. 1-Chloro-4-isocyanatobenzene (74.5 mg, 485 μmol) was added and the resulting mixture was stirred at room temperature overnight. The crude reaction mixture was concentrated in vacuo and purified on a silica column (hexane to 60% EtOAc/hexane gradient) to afford an oil. This oil was dissolved in ether and hexane and a 4N HCl solution (0.2 ml) was added and the mixture concentrated to afford 50 mg of (4-chlorophenyl)-carbamic acid (S)-1-(1,1-dioxo-1λ6-thiomorpholin-4-ylmethyl)-2,2,2-trifluoroethyl ester hydrochloride as a white solid. (M+H)+=401 m/e.

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. custompurified on a silica column (hexane to 60% EtOAc/hexane gradient)
  5. customto afford an oil
  6. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-ba4444a64410408ca224bef9d64216a6
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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