Sulfuryl chloride → HCID 59643143, compound

HRID 2251490Notes

Reaction equation

HRID 2251490 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)[CH2:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[N:7][CH:8]=1)[CH3:2].S(Cl)([Cl:36])(=O)=O>C(OCC)C>[Cl:36][C:18]1[CH:19]=[C:14]([C:11]([CH3:13])([CH3:12])[CH2:10][N:9]([C:6]2[N:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=2)[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:26][CH:27]=2)[CH:15]=[CH:16][C:17]=1[OH:20]

Participants

4

Reactant 2

HCID 24648Sulfuryl chloride2×HCID 46703408HCID 46703408, compound

Product 1

HCID 59643143HCID 59643143, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution 4-(2-{(5-ethylpyrimidin-2-yl)[4-(trifluoromethoxy)benzyl]amino}-1,1-dimethylethyl)phenol (300 mg; 0.67 mmol) in ethyl ether (0.1M) was added sulfuryl chloride (0.060 ml; 0.74 mmol). After 10 minutes an additional 0.3 eq of sulfuryl chloride were added. Stirred 20 more minutes. Partitioned between ethyl acetate and dilute sodium bicarbonate solution. Organic phase was washed with saturated brine, dried over sodium sulfate and concentrated. Purification by radial chromatography on silica gel using a dichloromethane-hexane gradient (30–90%) provided the title compound (80 mg; 25% yield).

Workup

  1. customPartitioned between ethyl acetate and dilute sodium bicarbonate solution
  2. washOrganic phase was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by radial chromatography on silica gel using a dichloromethane-hexane gradient (30–90%)

Sources & evidence

ORD record
ord-6a58ae31260647f2b04df876c46a2cef
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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