Dimethyl Sulfoxide → Dimethyl Sulfide

HRID 1531301Notes

Reaction equation

HRID 1531301 reaction equation
[CH3:1][O:2][C:3](=[O:15])[NH:4][C@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:14])[CH:11]=2)[CH2:6]1.[CH3:16][S:17]([CH3:19])=O.N1C=CC=CC=1.[CH3:26][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([C:43](Cl)=[O:44])[C:32]=1[C:33]1[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([NH:4][C@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:14][C:43]([C:31]3[C:32]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:40])([F:42])[F:41])=[CH:35][CH:34]=4)=[C:27]([CH3:26])[CH:28]=[CH:29][CH:30]=3)=[O:44])[CH:11]=2)[CH2:6]1)=[O:15].[CH3:16][S:17][CH3:19]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 110556396-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid chlorideHCID 11413084(R)-Methyl (5-amino-2,3-dihydro-1H-inden-2-yl)carbamate

Product 2

HCID 1068Dimethyl SulfideHCID 9869236(r)-6-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice bath cooled solution of (R)-(5-aminoindan-2-yl)-carbamic acid methyl ester (9.5 g, 46.1 mmol), ([α]D=−26.29° (c=9.87 mg/mL, DMSO); mp 144-145° C.) and pyridine (4.48 mL, 55.5 mmol) in 200 mL of methylene chloride is added 6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid chloride ( 80.5 mL of a 0.63 M solution in methylene chloride, 50.7 mmol). The reaction is stirred for 15 minutes at room temperature. The mixture is washed with 1N HCl, bicarbonate and brine. The organic layer is dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The product is purified by crystallization from ethyl acetate/hexanes (1:2) to give (R)-6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide as a crystalline solid, mp 112-114° C. [α]D=−12.85°, c=11.36 mg/mL DMS.

Workup

  1. washThe mixture is washed with 1N HCl, bicarbonate and brine
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe product is purified by crystallization from ethyl acetate/hexanes (1:2)

Sources & evidence

ORD record
ord-993606a201e84e4a9ceb930785f13034
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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