Methanol → HCID 53911013, compound

HRID 1284582Notes

Reaction equation

HRID 1284582 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:7]([O:10][N:11]=[C:12]([C:16]1[N:20]=[C:19]([NH2:21])[S:18][N:17]=1)[C:13]([OH:15])=[O:14])[CH:8]=[CH2:9].[CH3:22]O.[OH-].[Na+]>C(Cl)Cl.N1C=CC=CC=1.O>[CH2:7]([O:10][N:11]=[C:12]([C:16]1[N:20]=[C:19]([NH2:21])[S:18][N:17]=1)[C:13]([O:15][CH3:22])=[O:14])[CH:8]=[CH2:9]

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24819Phosphorus pentachlorideHCID 54172645HCID 54172645, compound

Product 1

HCID 53911013HCID 53911013, compoundYield 69.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To solution of phosphorus pentachloride (10.92 g) in methylene chloride (110 ml) was added 2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (11.4 g) under cooling at -20° C. and stirring, which was continued for 50 minutes at -15° to -5° C. To the mixture was dropped a solution of methanol (2.4 g) in pyridine (15.82 g) at -30° to -10° C. under stirring, which was continued for 20 minutes at -10° C. To the reaction mixture was dropped water (110 ml) and the mixture was adjusted to pH 2 with 1N aqueous sodium hydroxide and then stirred for 30 minutes at 0° C. The resulting precipitate was filtered, washed with water and dried to give methyl 2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetate (syn isomer) (8.40 g).

Workup

  1. stirringunder stirring
  2. waitwhich was continued for 20 minutes at -10° C
  3. stirringstirred for 30 minutes at 0° C
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e71e843ba07c4b51a778998049412383
Source dataset
uspto-grants-1986_01
Patent number
US04563449

Reaction notes

Loading…