Triethylamine → HCID 54247250, compound

HRID 580217Notes

Reaction equation

HRID 580217 reaction equation
C([O-])(=O)C.[C:5]([C:7](=[N:11][O:12][CH3:13])[C:8]([NH2:10])=[NH2+:9])#[N:6].C(N(CC)CC)C.BrBr.[C:23]([S-:25])#[N:24].[K+]>CO>[NH2:24][C:23]1[S:25][N:10]=[C:8]([C:7](=[N:11][O:12][CH3:13])[C:5]#[N:6])[N:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 86742227HCID 86742227, compound

Product 1

HCID 54247250HCID 54247250, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 2-cyano-2-methoxyiminoacetamidinium acetate (125 g, 0.672 mole) in CH3OH (1.25 L) were added dropwise triethylamine (234 ml, 1.68 mole) at -10° C., and subsequently Br2 (41.6 ml, 0.806 mole) over 20 minutes at -15° to -10° C., and the mixture was stirred for 20 minutes. To the mixture was added dropwise a solution of KSCN (78.3 g, 0.806 mole) in CH3OH (550 ml) over 1 hour at -15° to -10° C. After stirring at 0°-5° C. for 1 hour, the mixture was poured into ice-water (12 L) to form a crystalline precipitate, which was collected by filtration, washed with water and air-dried to give 120 g (98%) of the title compound. M.p. 263°-5° C. (dec.). The m.p. of the compound prepared by us is higher by about 60° C. than that given in the literature* [m.p. 210°-15° C. (dec.)], but our spectral and microanalytical data are consistent for the structure.

Workup

  1. stirringAfter stirring at 0°-5° C. for 1 hour
  2. customto form a crystalline precipitate, which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-b5b7bbeab4464fc9a470c1c9ea999652
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

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