Sulfuryl chloride → HCID 68656860, compound

HRID 1618930Notes

Reaction equation

HRID 1618930 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.S(Cl)([Cl:19])(=O)=O>C(O)(=O)C.C(OCC)(=O)C>[Cl:19][C:13]1[C:8]2[N:7]=[N:6][N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:9]=2[CH:10]=[CH:11][C:12]=1[O:14][CH3:15]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 686570341-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole

Product 1

HCID 68656860HCID 68656860, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole (10 g, 49 mmol) was dissolved in acetic acid (100 mL), cooled to 0° C. and treated with sulfuryl dichloride (4.8 mL, 59 mmol, 1.2 equiv) over three minutes. The mixture was warmed to ambient temperature over three hours and stirred for an additional 14 hours. The mixture was diluted with ethyl acetate and washed with aqueous saturated sodium bicarbonate. The organic layer was dried with magnesium sulfate, filtered and partially concentrated in vacuo to ˜30 mL, which was then treated with water. The resulting precipitate was filtered, collected and dried in vacuo, providing the titled compound.

Workup

  1. temperatureThe mixture was warmed to ambient temperature over three hours
  2. washwashed with aqueous saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationpartially concentrated in vacuo to ˜30 mL, which
  6. additionwas then treated with water
  7. filtrationThe resulting precipitate was filtered
  8. customcollected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-33b628f2bba64466aa1fb9b9b6524a82
Source dataset
uspto-grants-2014_07
Patent number
US08772276B2

Reaction notes

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