Hydrochloric Acid → HCID 88592485, compound

HRID 531159Notes

Reaction equation

HRID 531159 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([CH2:14][OH:15])[CH2:12][OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>N1C=CC=CC=1>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:13][CH2:12][CH:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 23366071HCID 23366071, compound

Product 1

HCID 88592485HCID 88592485, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 24 (6.43 g, 30.44 mmol) in pyridine (20 mL) was added dropwise to a solution of p-toluenesulfonyl chloride (14.51 g, 76.11 mmol) in pyridine (30 mL), with temperature being kept below 0° C. After complete addition, the reaction mixture was stirred at room temperature for 10 hours, and then it was poured into ice-cold aqueous 5 M HCl (100 mL). The aqueous phase was extracted with CH2Cl2 (3×100 mL). The combined organic phase was washed with brine (2×100 mL), dried over MgSO4, and evaporated under reduced pressure to afford pale yellow oil, which was crystallized from ethanol (100 mL) to give white solid 25 (14.08 g, 89% yield).

Workup

  1. custombeing kept below 0° C
  2. additionAfter complete addition
  3. extractionThe aqueous phase was extracted with CH2Cl2 (3×100 mL)
  4. washThe combined organic phase was washed with brine (2×100 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customto afford pale yellow oil, which
  8. customwas crystallized from ethanol (100 mL)

Sources & evidence

ORD record
ord-85c6adeba5fd4c449b596d7bca67fe17
Source dataset
uspto-grants-2016_05
Patent number
US09353120B2

Reaction notes

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