Dimethylformamide → HCID 15335365, compound

HRID 1449632Notes

Reaction equation

HRID 1449632 reaction equation
[Cl:1][CH:2]([F:16])[C:3]([S:6][C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)([F:5])[F:4].ClS([N:21]=[C:22]=O)(=O)=O.CN(C)C=O.C(OCC)(=O)C>C(#N)C>[Cl:1][CH:2]([F:16])[C:3]([S:6][C:7]1[NH:8][C:9]2[C:14]([C:15]=1[C:22]#[N:21])=[CH:13][CH:12]=[CH:11][CH:10]=2)([F:4])[F:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 70918Chlorosulfonyl isocyanateHCID 15335347HCID 15335347, compound

Product 1

HCID 15335365HCID 15335365, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2-[(2-chloro-1,1,2-trifluoroethyl)thio]indole (0.64 g, 2.4 mmole) in acetonitrile is treated with a solution of chlorosulfonylisocyanate (CSI) (0.85 g, 6.0 mmole) in acetonitrile at ice bath temperatures, stirred at room temperature for 3 hours, treated with dimethylformamide (0.88 g, 12 mmole) at 0° C., stirred for 1 hour at ambient temperatures, poured into ice water and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to give a residue. Flash chromatography (silica gel/1:4 ethyl acetate:hexanes) affords the title product as a white solid, 0 44 g (63% yield) mp 134°-136° C. identified by IR, 1HNMR and 13CNMR.

Workup

  1. stirringstirred for 1 hour at ambient temperatures
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-74896821c7e645198a29a549f3d9aef6
Source dataset
uspto-grants-1997_02
Patent number
US05599832

Reaction notes

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