Triethylamine → HCID 54374598, compound

HRID 2412858Notes

Reaction equation

HRID 2412858 reaction equation
C(O)(=O)C.[C:5]([C:7](=[N:11][O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:8]([NH2:10])=[NH:9])#[N:6].C(N(CC)CC)C.BrBr.[S-:27][C:28]#[N:29].[K+]>CO>[CH3:17][O:16][C:14]([CH2:13][O:12][N:11]=[C:7]([C:8]1[N:10]=[C:28]([NH2:29])[S:27][N:9]=1)[C:5]#[N:6])=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 86739873HCID 86739873, compound

Product 1

HCID 54374598HCID 54374598, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 2-cyano-2-methoxycarbonylmethoxyiminoacetamidine acetate (495 g) in methanol (4.95 l) was dropped triethylamine (512.6 g) at -10° C. under stirring and cooling, and further, bromine (357.3 g) was added to the above mixture at the same temperature. After the reaction mixture was stirred for 15 minutes, a solution of potassium thiocyanate (216 g) in methanol (2.16 l) was dropped thereto at -10° to -5° C. under stirring, which was continued for 30 minutes at 0° to 5° C. The resulting precipitates were collected by filtration, washed with water (5 l) and dried to give 2-methoxycarbonylmethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetonitrile (syn isomer) (430 g), which was recrystallized from aqueous methanol, mp. 225° to 227° C. (dec.).

Workup

  1. temperaturecooling
  2. stirringAfter the reaction mixture was stirred for 15 minutes
  3. stirringat -10° to -5° C. under stirring
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water (5 l)
  7. customdried

Sources & evidence

ORD record
ord-116b926eb9c64945bb5908981d8b11f9
Source dataset
uspto-grants-1985_01
Patent number
US04495182

Reaction notes

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