Hydrochloric Acid → HCID 74088770, compound

HRID 622758Notes

Reaction equation

HRID 622758 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:11]1[N:15]=[C:14]([NH:16][P:17]([O:21][CH3:22])([O:19][CH3:20])=[O:18])[S:13][N:12]=1)[C:7]([O:9]C)=[O:8])[CH:2]=[CH2:3].[OH-].[Na+:24].Cl>O1CCCC1>[CH2:1]([O:4][N:5]=[C:6]([C:11]1[N:15]=[C:14]([NH:16][P:17]([O:19][CH3:20])([O:21][CH3:22])=[O:18])[S:13][N:12]=1)[C:7]([O-:9])=[O:8])[CH:2]=[CH2:3].[Na+:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53935379HCID 53935379, compound

Product 1

HCID 74088770HCID 74088770, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-allyloxyimino-2-(5-dimethoxyphosphorylamino-1,2,4-thiadiazol-3-yl)acetate (syn isomer) (37.3 g) in tetrahydrofuran (106 ml) was added 1N-aqueous sodium hydroxide (234 ml) and the mixture was stirred for 2 hours at ambient temperature. The reaction mixture was adjusted to pH 5 with 6N hydrochloric acid and washed with ethyl acetate. The aqueous layer was separated out, adjusted to pH 1.0 with 6N hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated. The residue dissolved in methanol (50 ml) was added dropwise to a solution of sodium acetate (8.7 g) in methanol (90 ml) at ambient temperature under stirring, which was continued for one hour at the same temperature. To the mixture was added ethyl acetate (200 ml) and the resulting precipitate was collected by filtration, washed with ethyl acetate and dried to give sodium 2-allyloxyimino-2-(5-dimethoxyphosphorylamino-1,2,4-thiadiazol-3-yl)acetate (syn isomer) (32.6 g), mp. 168° to 173° C. (dec.).

Workup

  1. washwashed with ethyl acetate
  2. customThe aqueous layer was separated out
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue dissolved in methanol (50 ml)
  8. additionwas added dropwise to a solution of sodium acetate (8.7 g) in methanol (90 ml) at ambient temperature
  9. stirringunder stirring
  10. waitwhich was continued for one hour at the same temperature
  11. additionTo the mixture was added ethyl acetate (200 ml)
  12. filtrationthe resulting precipitate was collected by filtration
  13. washwashed with ethyl acetate
  14. customdried

Sources & evidence

ORD record
ord-8b34b6ac19ed443e8d2bca1f72390d98
Source dataset
uspto-grants-1988_09
Patent number
US04772682

Reaction notes

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