Lithium Hydroxide → 2-(4-Methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetic acid

HRID 1522067Notes

Reaction equation

HRID 1522067 reaction equation
[CH3:1][CH:2]1[CH2:7][N:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[S:5](=[O:18])(=[O:17])[N:4]([CH2:19][C:20]([O:22]C)=[O:21])[CH2:3]1.[Li+].[OH-]>C1COCC1.CO.O>[CH3:1][CH:2]1[CH2:7][N:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[S:5](=[O:17])(=[O:18])[N:4]([CH2:19][C:20]([OH:22])=[O:21])[CH2:3]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86708915Methyl 2-(4-methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetate

Product 1

HCID 867089162-(4-Methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetic acidYield 95.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 2-(4-methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetate (2.3 g, 5.4 mmol) in THF (12 mL) and MeOH (12 mL), was dropwisely added LiOH (1.1 g, 27.0 mmol) in H2O. The reaction mixture was agitated for 3 hr at room temperature. After the completion of the reaction, the resultant was concentrated and its pH was adjusted down to 3 with 2 N HCl after the addition of water. The resultant was extracted with EtOAc, dried over Na2SO4, filtered and concentrated under reduced pressure, giving the title compound (2.0 g, y=83%, solid). 1H NMR (300 MHz, CDCl3) δ 7.42 (d, J=2.4 Hz, 1H), 7.38 (d, J=2.4 Hz, 1H), 4.53 (d, J=17 Hz, 1H), 4.16-3.88 (m, 4H), 3.40-3.38 (m, 1H), 3.20-3.15 (m, 1H), 2.57-2.11 (m, 1H), 0.93 (d, J=7.1 Hz, 3H).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe resultant was concentrated
  3. additionafter the addition of water
  4. extractionThe resultant was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b68d6403e40c425eb28bc5233566b791
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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