Phthalic Acid → HCID 54570443, compound

HRID 1031213Notes

Reaction equation

HRID 1031213 reaction equation
C(O)(=O)C1C(=CC=CC=1)C(O)=O.[C:13]([C:15](=[N:19][O:20][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:23])[CH3:22])[C:16]([NH2:18])=[NH:17])#[N:14].BrBr.[S-:31][C:32]#[N:33].[K+]>CO.O.CN(C)C=O.C(N(CC)CC)C>[NH2:33][C:32]1[S:31][N:18]=[C:16]([C:15](=[N:19][O:20][C:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:23])[CH3:22])[C:13]#[N:14])[N:17]=1

Participants

9

Reactant 4

HCID 1017Phthalic AcidHCID 24408BromineHCID 516872Potassium thiocyanateHCID 53744657HCID 53744657, compound

Product 1

HCID 54570443HCID 54570443, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of phthalic acid salt (10.0 g) of 2-cyano-2-(1-ethoxycarbonyl-1-methylethoxyimino)acetamidine in methanol (60 ml) were added dropwise triethylamine (9.01 g) and bromine (3.67 g) at -15°~-10° C. After stirring for 15 minutes at the same temperature, N,N-dimethylformamide (6.0 ml) and a solution of potassium thiocyanate (2.23 g) in methanol (22.3 ml) were added dropwise thereto at -15°~-10° C. After stirring for one hour at -5°~0° C., the solution was poured into cold water (300 ml) and the mixture was stirred for one hour under ice-cooling. The resulting precipitate was collected by filtration, washed with cold water (60 ml) and dried under reduced pressure to give 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-ethoxycarbonyl-1-methylethoxyimino)acetonitrile (3.82 g).

Workup

  1. customat -15°~-10° C
  2. stirringthe mixture was stirred for one hour under ice-
  3. temperaturecooling
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with cold water (60 ml)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-061f0dd8794549a98d28b607b603a59a
Source dataset
uspto-grants-1992_04
Patent number
US05108997

Reaction notes

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