Stannous chloride dihydrate → HCID 16045450, compound

HRID 658274Notes

Reaction equation

HRID 658274 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[S:11]([N:14]([CH:28]([CH3:30])[CH3:29])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)(=[O:13])=[O:12].O.O.Cl[Sn]Cl>CCO>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([S:11]([N:14]([CH:28]([CH3:29])[CH3:30])[C:15]2[CH:16]=[CH:17][C:18]([C:21]([OH:27])([CH3:26])[C:22]([F:25])([F:23])[F:24])=[CH:19][CH:20]=2)(=[O:13])=[O:12])[CH:4]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 16045526HCID 16045526, compound

Product 1

HCID 16045450HCID 16045450, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 2-chloro-N-isopropyl-5-nitro-N-[4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl]benzenesulfonamide (11) (704 mg, 1.50 mmol, 1.0 equiv) in EtOH (40 mL) was treated with SnCl2.2H2O (1.70 g, 7.50 mmol, 5.0 equiv). After stirring at 75° C. for 2 h, the reaction mixture was concentrated under reduced pressure, diluted (EtOAc) and washed (3×1 M aqueous NaOH and 1×brine). The organics were dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue (SiO2, 30-40% EtOAc/Hexane, gradient elution) gave the product as a white foam. 1H NMR (DMSO-d6, 500 MHz) δ 7.59 (d, J=8.6 Hz, 2H), 7.28 (d, J=8.6 Hz, 1H), 7.12 (d, J=8.6 Hz, 2H), 7.08 (d, J=2.8 Hz, 1H), 6.73 (dd, J=2.8, 8.6 Hz, 1H), 6.65 (s, 1H), 5.67 (s, 1H), 4.50-4.42 (m, 1H), 1.67 (s, 3H), 1.04 (d, J=6.6 Hz, 3H), 1.03 (d, J=6.6 Hz, 3H). MS (ESI) 437 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additiondiluted (EtOAc)
  3. washwashed (3×1 M aqueous NaOH and 1×brine)
  4. dry with materialThe organics were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. washFlash chromatography of the residue (SiO2, 30-40% EtOAc/Hexane, gradient elution)

Sources & evidence

ORD record
ord-8a7e14a6385149e4a4e286dfcc0ddc3d
Source dataset
uspto-grants-2011_12
Patent number
US08076376B2

Reaction notes

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