4-Toluenesulfonyl chloride → HCID 11015881, compound

HRID 2168168Notes

Reaction equation

HRID 2168168 reaction equation
C(N([CH2:6][CH3:7])CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[CH2:19]1[O:23][C@@H:22]2[C@@H:24]([OH:27])[CH2:25][O:26][C@@H:21]2[C@@H:20]1[OH:28]>ClCCl>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:28][C@@H:20]2[CH2:19][O:23][C@@H:22]3[C@@H:24]([O:27][S:14]([C:11]4[CH:12]=[CH:13][C:6]([CH3:7])=[CH:9][CH:10]=4)(=[O:16])=[O:15])[CH2:25][O:26][C@H:21]23)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 12597Isosorbide

Product 1

HCID 11015881HCID 11015881, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Triethylamine (123.2 mL, 876 mmol) was added dropwise to a stirred solution of p-toluenesulfonyl chloride (156.6 g, 822 mmol) and isosorbide (43) (40 g, 274 mmol) in dichloromethane (600 mL) over 15 minutes. The mixture was stirred at 25° C. for 16 hours then at 50° C. for 4 hours before diluting with dichloromethane (1 L). The organic layer was washed with water (2×1 L), then dried (Na2SO4), filtered then reduced in vacuo to leave a viscous oil. The oil was crystallized from hot methanol (600 mL) to obtain ditosylate (42) as a white solid (120.1 g, 97%). [α]D15+56.3° (c=11.2, CHCl3).

Workup

  1. washThe organic layer was washed with water (2×1 L)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customto leave a viscous oil
  5. customThe oil was crystallized from hot methanol (600 mL)

Sources & evidence

ORD record
ord-e35afa2c6fa84e139a62f158a5fc22f3
Source dataset
uspto-grants-2015_06
Patent number
US09045492B2

Reaction notes

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