HCID 178503843, compound → HCID 178503880, compound

HRID 1732019Notes

Reaction equation

HRID 1732019 reaction equation
[NH:1]([C:5]1[S:6][C:7]2[CH2:8][NH:9][CH2:10][CH2:11][C:12]=2[N:13]=1)[C:2]([NH2:4])=[NH:3].[C:14]([N:16]=[C:17]([S-])[S-:18](C)[CH3:19])#[N:15]>C(O)C>[NH:1]([C:5]1[S:6][C:7]2[CH2:8][N:9]([C:17]([S:18][CH3:19])=[N:16][C:14]#[N:15])[CH2:10][CH2:11][C:12]=2[N:13]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 178503843HCID 178503843, compoundHCID 178512601HCID 178512601, compound

Product 1

HCID 178503880HCID 178503880, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3.95 g (20 mmol) of 2-guanidino-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine in 40 ml of absolute ethanol, 3.51 g (24 mmol) of N-cyano-S,S-dimethyldithioimidocarbonate (IV: X"=NR8, R8 =CN) was added at room temperature. After standing for 30 hours, the reaction mixture was evaporated to dryness and the crude residue was chromatographed on a silica gel column using ethyl acetate with increasing methanol as eluant. 4.7 g (80% yield) of 2-guanidino-5-(methylthio-N-cyano-imino-methyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (V: ##STR15## R2 =R6 =R7 =H, n=0, X"=NR8, R8 =CN), m.p. 224°-227° C., were obtained. This compound was treated with a 33% solution of methylamine in 93 ml of ethanol at room temperature. After standing for 24 hours the solid compound was filtered and crystallized from methanol. 2.21 g (50% yield) of the title compund (m.p. 243°-246° C. with decomposition) were obtained.

Workup

  1. additionwas added at room temperature
  2. customthe reaction mixture was evaporated to dryness
  3. customthe crude residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-e4ddb39ec71b4e2ab6767a53a4fe488b
Source dataset
uspto-grants-1986_11
Patent number
US04624956

Reaction notes

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