Diisobutylamine → HCID 68698119, compound

HRID 1172822Notes

Reaction equation

HRID 1172822 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:17]4[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:16]=4[O:15][N:14]=3)=[C:9]([CH2:23][CH2:24][CH3:25])[CH:8]=2)=[CH:4][CH:3]=1.C(NCC(C)C)C(C)C.S(Cl)([Cl:40])(=O)=O>C1(C)C=CC=CC=1>[Cl:40][C:18]1[C:17]2[C:13]([C:10]3[CH:11]=[CH:12][C:7]([O:6][C:5]4[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=4)=[CH:8][C:9]=3[CH2:23][CH2:24][CH3:25])=[N:14][O:15][C:16]=2[CH:21]=[CH:20][C:19]=1[OH:22]

Participants

5

Reactant 3

HCID 8085DiisobutylamineHCID 24648Sulfuryl chlorideHCID 68691874HCID 68691874, compound

Product 1

HCID 68698119HCID 68698119, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of the phenol product obtained from step 6 of Example 3 (0.38 g, 1.0 mmol) and diisobutylamine (18 μL, 0.10 mmol) in toluene (5 mL) was added dropwise sulfuryl chloride (80 μL, 1.0 mmol) over 10 min. The resulting solution was stirred at 25° C. for 1 h and then quenched with a saturated solution of aqueous sodium bicarbonate. The organic layer was extracted with ethyl acetate and the combined organic layer was washed with 2 N solution of sodium sulfite. After removal of the solvent, the crude product was purified by chromatography on silica gel eluting with 7:3 hexane:ethyl acetate to give the title product as a solid.

Workup

  1. customquenched with a saturated solution of aqueous sodium bicarbonate
  2. extractionThe organic layer was extracted with ethyl acetate
  3. washthe combined organic layer was washed with 2 N solution of sodium sulfite
  4. customAfter removal of the solvent
  5. customthe crude product was purified by chromatography on silica gel eluting with 7:3 hexane

Sources & evidence

ORD record
ord-aa567c8373764acb86a6f72e5619b3f8
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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