Ammonium Chloride → HCID 86691229, compound

HRID 1483022Notes

Reaction equation

HRID 1483022 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[Br:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[N:17]\[S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])=[CH:12][CH:11]=1.[Cl-].[NH4+]>C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C@H:16]([NH:17][S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[C:2]([F:4])([F:3])[F:1])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 89713970HCID 89713970, compound

Product 1

HCID 86691229HCID 86691229, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 82707Tetrabutylammonium AcetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

Add neat (trifluoromethyl)trimethylsilane (109 mL, 0.74 mol) to a stirred solution of tetrabutylammonium acetate (88 g, 0.29 mol) and (N—Z)—N-[(4-bromophenyl)methylene]-(R)-2-methyl-propane-2-sulfinamide (85 g, 0.29 mol) in DMF (1.2 L) at 0° C. Stir the mixture at 0-5° C. for 90 min Add a saturated aqueous ammonium chloride solution (1.2 L) and extract with EtOAc (4×400 mL). Combine the organic extracts; sequentially wash the extracts with water then brine (2×1 L); dry over MgSO4; filter; and concentrate the filtrate under reduced pressure. Triturate the residue with hexane (200 mL) for 10 min; filter; and dry under reduced pressure to afford the title compound as a yellow solid (81 g, 76% yield, >98 de). MS (m/z): 358 (M+1).

Workup

  1. extractionextract with EtOAc (4×400 mL)
  2. washsequentially wash the extracts with water
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationand concentrate the filtrate under reduced pressure
  6. customTriturate the residue with hexane (200 mL) for 10 min
  7. filtrationfilter
  8. customand dry under reduced pressure

Sources & evidence

ORD record
ord-3480e3c6b42e4e30b6da1e02cc44bfa4
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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