Methanol → HCID 178503180, compound

HRID 1835972Notes

Reaction equation

HRID 1835972 reaction equation
Cl.[Cl:2][C:3]1[C:8]([S:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:11][C:12]([N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S@@:22]([CH3:24])=[O:23])[CH:17]=1)[CH3:15])=[NH:13].CO.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:2][C:3]1[C:8]([S:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:11][C:12]([N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S@@:22]([CH3:24])=[O:23])[CH:17]=1)[CH3:15])=[NH:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 178503181HCID 178503181, compound

Product 1

HCID 178503180HCID 178503180, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Conversion of the Hydrochloride Salt to the Free Base (R)-N-(2-chloro-3-methylthiophenyl)-N′-(3-methylsulfinylphenyl)-N′-methylguanidine hydrochloride (0.56 g) was dissolved in chloroform (25 ml) and methanol (3 ml) added to get a clear solution and this was treated with sodium hydroxide (1N, 2×25 ml) in a separating funnel. The organic layer was separated and the aqueous layer was extracted with chloroform (20 ml). Combined organic layer was washed with water (25 ml) and passed through a bed of sodium chloride to remove any solid suspensions and the filtrate was concentrated to yield the free base of (R)-N-(2-chloro-3-methylthiophenyl)-N′-(3-methylsulfinylphenyl)-N′-methylguanidine (0.37 g., 73%); Chiral HPLC 76.5% ee @ 16.45; HPLC 97.7% @ 14.5 mins; 1H-NMR (CD3OD) δ 2.46 (s, 3H, SMe), 2.77 (s, 3H, S(O)Me), 3.47 (s, 3H, NMe), 6.81 (dd, 1H), 6.87 (dd, 1H), 7.28 (d, 1H), 7.50 (m, 3H), 7.68 (s, 1H).

Workup

  1. customto get a clear solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform (20 ml)
  4. washCombined organic layer was washed with water (25 ml)
  5. customto remove any solid suspensions
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b9a1232683154dd2b52692ad5ed59223
Source dataset
uspto-grants-2004_08
Patent number
US06774263B1

Reaction notes

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