Dichloromethane → HCID 59260561, compound

HRID 643217Notes

Reaction equation

HRID 643217 reaction equation
S([Cl:11])(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C.[F:19][C:20]([F:36])([F:35])[C:21]1[CH:26]=[C:25]([CH2:27]O)[C:24]([C:29]([F:32])([F:31])[F:30])=[CH:23][C:22]=1CO.Cl[CH2:38][Cl:39]>CN(C)C1C=CN=CC=1>[F:19][C:20]([F:36])([F:35])[C:21]1[CH:26]=[C:25]([CH2:27][Cl:11])[C:24]([C:29]([F:32])([F:31])[F:30])=[CH:23][C:22]=1[CH2:38][Cl:39]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 59260569HCID 59260569, compound

Product 1

HCID 59260561HCID 59260561, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

Tosyl chloride (3.9 g, 20.4 mmol), 4-dimethylaminopyridine (936.3 mg, 7.7 mmol), and distilled triethylamine (1.73 mL, 12.4 mmol) were added sequentially to a solution of compound 3 in dichloromethane (30 mL) under Ar at room temperature. The reaction mixture was stirred at this temperature for 4 h. The resulting solution was evaporated and the residue was diluted with hexane (100 mL). The organic layer was washed with water (3×50 mL), dried over anhydrous MgSO4, evaporated, and purified by column chromatography (hexane as eluant) to give product 5 as a white solid (700 mg, 62%); 1H NMR (300 MHz, CDCl3): 7.98 (2H, s), 4.78 (4H, s); 19F NMR (282 MHz, CDCl3): −60.6; HR-MS (EI) calcd. for C10H6F6Cl2 (M+): 309.9745, found: 309.9738.

Workup

  1. customThe resulting solution was evaporated
  2. additionthe residue was diluted with hexane (100 mL)
  3. washThe organic layer was washed with water (3×50 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated
  6. custompurified by column chromatography (hexane as eluant)

Sources & evidence

ORD record
ord-cf5ac12bc37c4aedbec951994bf959b9
Source dataset
uspto-grants-2010_04
Patent number
US07700366B2

Reaction notes

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