Ethanol → HCID 54112149, compound

HRID 1907035Notes

Reaction equation

HRID 1907035 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:11]1[N:15]=[C:14]([NH:16][P:17](Cl)(Cl)=[O:18])[S:13][N:12]=1)[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3].N1[CH:26]=[CH:25]C=CC=1.[CH2:27]([OH:29])[CH3:28].[OH2:30]>C(Cl)Cl>[CH2:1]([O:4][N:5]=[C:6]([C:11]1[N:15]=[C:14]([NH:16][P:17]([O:18][CH2:25][CH3:26])([O:29][CH2:27][CH3:28])=[O:30])[S:13][N:12]=1)[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1049PyridineHCID 53963231HCID 53963231, compound

Product 1

HCID 54112149HCID 54112149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-allyloxyimino-2-(5-dichlorophosphorylamino-1,2,4-thiadiazol-3yl)acetate (syn isomer) (5.0 g) in methylene chloride (100 ml) were successively added pyridine (3.3 g) and a solution of ethanol in methylene chloride (100 ml) under cooling at -35° C. to -25° C. and stirring. The mixture was stirred for 20 minutes at -20° to -10° C., for 30 minutes at 5° C. and then for two hours at room temperature, and poured into water (100 ml). The organic layer was separated, washed with 1N aqueous hydrochloric acid and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to dryness under reduced pressure to give methyl 2-allyloxyimino-2-(5-diethoxyphosphorylamino-1,2,4-thiadiazol-3-yl)acetate (syn isomer) (5.25 g) as yellow oil.

Workup

  1. stirringThe mixture was stirred for 20 minutes at -20° to -10° C., for 30 minutes at 5° C.
  2. customThe organic layer was separated
  3. washwashed with 1N aqueous hydrochloric acid
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7d576f2747894230b867c28007a96910
Source dataset
uspto-grants-1987_03
Patent number
US04654422

Reaction notes

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