Sodium Hydroxide → 2-(2,6-Dichloro-4-(trifluoromethyl)phenyl)-4-methyl-1,2,6-thiadiazinan 1,1-dioxide

HRID 1522080Notes

Reaction equation

HRID 1522080 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[S:18](=[O:20])(=[O:19])[N:17](C(OC)=O)[CH2:16][CH:15]([CH3:25])[CH2:14]1.[OH-].[Na+]>CO>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[CH2:14][CH:15]([CH3:25])[CH2:16][NH:17][S:18]1(=[O:19])=[O:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708927Methyl 6-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-methyl-1,2,6-thiadiazinan-2-carboxylate 1,1-dioxide

Product 1

HCID 867089282-(2,6-Dichloro-4-(trifluoromethyl)phenyl)-4-methyl-1,2,6-thiadiazinan 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 6-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-methyl-1,2,6-thia-diazinan-2-carboxylate 1,1-dioxide (3.58 g, 8.50 mmol) in MeOH (60 mL), was dropwisely added 1 N NaOH (85 mL, 85 mmol) and agitated for 12 hr at room temperature. Following concentration under reduced pressure, ethyl acetate (30 mL) and water (30 mL) were added to the resultant to obtain the organic layer. The organic layer was dried over MgSO4 and crystallized using ethyl acetate (10 mL) and hexane (70 mL), giving the compound of interest (2.96 g, 96%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.65 (s, 2H), 4.48-4.43 (m, 1H), 4.04-3.96 (m, 1H), 3.61-3.55 (m, 2H), 3.42-3.36 (m, 1H), 2.32 (m, 1H), 0.97 (d, 3H, J=6.8 Hz).

Workup

  1. concentrationconcentration under reduced pressure, ethyl acetate (30 mL) and water (30 mL)
  2. additionwere added to the resultant
  3. customto obtain the organic layer
  4. dry with materialThe organic layer was dried over MgSO4
  5. customcrystallized
  6. customgiving the compound of interest (2.96 g, 96%, white solid)

Sources & evidence

ORD record
ord-e418ab2ac06a47dbb94ce89465f1fa89
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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