Triethylamine → HCID 54570443, compound

HRID 373433Notes

Reaction equation

HRID 373433 reaction equation
C(O)(=O)C.[C:5]([C:7](=[N:11][O:12][C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:15])[CH3:14])[C:8]([NH2:10])=[NH:9])#[N:6].C(N(CC)CC)C.BrBr.[S-:30][C:31]#[N:32].[K+]>CO.O.CN(C)C=O>[NH2:32][C:31]1[S:30][N:10]=[C:8]([C:7](=[N:11][O:12][C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:15])[CH3:14])[C:5]#[N:6])[N:9]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 86743945HCID 86743945, compound

Product 1

HCID 54570443HCID 54570443, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-cyano-2-(1-ethoxycarbonyl-1-methylethoxyimino)acetamidine acetate (685 g) in methanol (6.85 l) was added triethylamine (557 g) at -13°~15° C. over a 20-minute period and then bromine (344 g) was added thereto at the same temperature over the same period. The solution was stirred at -13°~15° C. for 15 minutes, then N,N-dimethylformamide (685 ml) was added to the solution at the same temperature, and a solution of potassium thiocyanate (209 g) in methanol (2.09 l) was added thereto at -13°~15° C. over a 30-minute period. After being stirred at -5°~0° C. for an hour, the solution was poured into a cold water (5°~10° C.) and stirred for an hour under ice-cooling. The resulting precipitates were collected by filtration, washed with cold water and dried to give 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-ethoxycarbonyl-1-methylethoxyimino)acetonitrile (390 g).

Workup

  1. waitat -13°~15° C. over a 30-minute period
  2. stirringAfter being stirred at -5°~0° C. for an hour
  3. stirringstirred for an hour under ice-
  4. temperaturecooling
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with cold water
  8. customdried

Sources & evidence

ORD record
ord-7d6c901e784c4f0bb5b2561baf52d60a
Source dataset
uspto-grants-1992_11
Patent number
US05162520

Reaction notes

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