Triethylamine → HCID 77230708, compound

HRID 1508515Notes

Reaction equation

HRID 1508515 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[C:8]([CH2:16]O)=[N:9][C:10]([S:14][CH3:15])=[N:11][C:12]=1[CH3:13].CCN(CC)CC>C(Cl)Cl>[Cl:6][C:7]1[C:12]([CH3:13])=[N:11][C:10]([S:14][CH3:15])=[N:9][C:8]=1[CH2:16][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68080203HCID 68080203, compound

Product 1

HCID 77230708HCID 77230708, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

MsCl (248 mg, 2.169 mmol) was added to a stirred, cooled 0° C. mixture of the title compound from Step D (370 mg, 1.808 mmol) in CH2Cl2 (10 mL), followed by addition of Et3N (274 mg, 2.71 mmol). The mixture was stirred at 0° C. for 30 min. TLC showed no starting material left. The mixture was quenched with water (5 mL) and the mixture was washed with more water (10 mL). The organic fraction were washed with brine (saturated, 10 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with EtOAc/hexane (2/8) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 5.40 (s, 2H), 3.20 (s, 3H), 2.61 (s, 3H), 2.59 (s, 3H).

Workup

  1. waitleft
  2. customThe mixture was quenched with water (5 mL)
  3. washthe mixture was washed with more water (10 mL)
  4. washThe organic fraction were washed with brine (saturated, 10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel Biotage 40S
  9. washeluting with EtOAc/hexane (2/8)

Sources & evidence

ORD record
ord-1848cc41273e4f8aaa674f5077843cef
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

Loading…