Hydrochloric Acid → HCID 86708919, compound

HRID 1522070Notes

Reaction equation

HRID 1522070 reaction equation
[CH2:1]=[C: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]CC)=[O:21])[CH2:3]1.C(OCC)(=O)C.Cl>C1COCC1.CO.O>[CH2:1]=[C: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

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86708917HCID 86708917, compound

Product 1

HCID 86708919HCID 86708919, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 2-(4-methylene-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetate (305 mg, 0.74 mmol) in THF (10 mL) and MeOH (10 mL), was added LiOH monohydrate (155 mg, 3.69 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 the organic layer. The resultant was dried over MgSO4, concentrated under reduced pressure, and crystallized with ethyl acetate (1 mL) and hexane (10 mL), giving the compound of interest (253 mg, 89%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.42 (s, 2H), 5.26 (s, 1H), 5.16 (s, 1H), 4.41 (s, 2H), 4.33 (s, 2H), 4.09 (s, 2H).

Workup

  1. extractionextracted to the organic layer
  2. dry with materialThe resultant was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customcrystallized with ethyl acetate (1 mL) and hexane (10 mL)
  5. customgiving the compound of interest (253 mg, 89%, white solid)

Sources & evidence

ORD record
ord-0a20bf8b96ef463e88a45783c84f668e
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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