Triethylamine → HCID 20341463, compound

HRID 1395039Notes

Reaction equation

HRID 1395039 reaction equation
Cl[C:2]1[C:7](=[O:8])[C:6]([Cl:9])=[N:5][S:4][N:3]=1.[C:10]([CH:12]([OH:26])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1)#[N:11].C(N(CC)CC)C.Cl.C(N(CC)CC)C>C(OCC)(=O)C.O>[Cl:9][C:6]1[C:7](=[O:8])[C:2]([O:26][CH:12]([C:10]#[N:11])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:14]=2)=[N:3][S:4][N:5]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 3540263,5-Dichloro-4H-1,2,6-thiadiazin-4-one

Product 1

HCID 20341463HCID 20341463, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of 7.3 grams (0.04 mole) of 3,5-dichloro-4H-1,2,6-thiadiazin-4-one and 9.0 grams (0.04 mole) of a α-cyano-3-phenoxybenzyl alcohol in 130 ml of ethyl acetate was added dropwise a solution of 4.1 grams (0.04 mole) of triethylamine in approximately 40 ml of ethyl acetate. Upon complete addition the reaction mixture was stirred at ambient temperature for 16 hours, then diluted with 100 ml of water to dissolve triethylamine hydrochloride. The organic layer was removed and washed with 100 ml of water, then with 100 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to a residual solid. The solid was triturated with absolute ethanol and collected by filtration. The filter cake was washed with hexane and recrystallized from glacial acetic acid. The yield was 5.8 grams (39%) of 3-chloro-5-(α-cyano-3-phenoxybenzyloxy)-4H-1,2,6-thiadiazin-4-one; m.p. 146.5°-147.7° C. The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. additionUpon complete addition the reaction mixture
  2. customThe organic layer was removed
  3. washwashed with 100 ml of water
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure to a residual solid
  7. customThe solid was triturated with absolute ethanol
  8. filtrationcollected by filtration
  9. washThe filter cake was washed with hexane
  10. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-b35dacda7cc84ed39034fd21cd3bac59
Source dataset
uspto-grants-1980_05
Patent number
US04201780

Reaction notes

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