Hydrochloric Acid → HCID 86708933, compound

HRID 1522084Notes

Reaction equation

HRID 1522084 reaction equation
[F:1][C:2]1([F:25])[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]CC)=[O:21])[CH2:3]1.C(OCC)(=O)C.Cl>C1COCC1.CO.O>[F:25][C:2]1([F:1])[CH2:7][N:6]([C:8]2[C:9]([Cl:16])=[CH:10][C:11]([Cl:15])=[CH:12][C:13]=2[Cl:14])[S:5](=[O:18])(=[O:17])[N:4]([CH2:19][C:20]([OH:22])=[O:21])[CH2:3]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86708934HCID 86708934, compound

Product 1

HCID 86708933HCID 86708933, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 2-(4,4-difluoro-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetate (40 mg, 0.10 mmol) in THF (10 mL) and MeOH (10 mL), was dropwisely added LiOH monohydrate (21 mg, 0.50 mmol) in water (3 mL) and agitated for 5 hr at room temperature. After addition of ethyl acetate (30 mL) and water (30 mL), pH of the resultant was adjusted to 3 with 1 N HCl and extracted to obtain the organic layer. The organic layer was dried over MgSO4, concentrated under reduced pressure, and crystallized with ethyl acetate (1 mL) and hexane (10 mL), giving the compound of interest (33 mg, 80%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.44 (s, 2H), 4.35 (s, 2H), 4.14-4.03 (m, 4H).

Workup

  1. extractionextracted
  2. customto obtain the organic layer
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customcrystallized with ethyl acetate (1 mL) and hexane (10 mL)
  6. customgiving the compound of interest (33 mg, 80%, white solid)

Sources & evidence

ORD record
ord-e503e21fb0de4f7684f3d69f9c3d8986
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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