Thiophosgene → HCID 10287273, compound

HRID 895132Notes

Reaction equation

HRID 895132 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]=[N:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:19][CH2:18][S:17](=[NH:20])[CH2:16][CH2:15]3)=[C:10]([F:21])[CH:9]=2)[CH:7]=1.[C:22](=O)(O)[O-:23].[Na+].[C:27](Cl)(Cl)=[S:28]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:22][O:23][C:27](=[S:28])[NH:1][CH2:2][C:3]1[N:4]=[N:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:15][CH2:16][S:17](=[NH:20])[CH2:18][CH2:19]3)=[C:10]([F:21])[CH:9]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 10193183HCID 10193183, compound

Product 1

HCID 10287273HCID 10287273, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled solution of the 4-[4-(4-aminomethyl-[1,2,3]triazol-1-yl)-2-fluoro-phenyl]-1-imino-1lambda*4*-thiomorpholine (100 mg, 0.3 mmol), obtained in Example 32 in CHCl3 (10 ml) was added sat. sodium bicarbonate solution followed by thiophosgene (36 μl, 0.33 mmol). The reaction mixture was stirred at room temperature for 0.5 h and then diluted with ethyl acetate (30 ml). The organic portion was washed with water followed by brine and dried over sodium sulfate. Evaporation of volatiles left a residue, which was refluxed with methanol (20 ml) for 20 h. Removal of volatiles and purification of the resulting residue by silica gel column chromatography (CHCl3/MeOH, 1:4) yielded the title compound as white solid (70 mg, 71%). Mp. 198° C.

Workup

  1. washThe organic portion was washed with water
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of volatiles
  4. waitleft a residue, which
  5. temperaturewas refluxed with methanol (20 ml) for 20 h
  6. customRemoval of volatiles and purification of the resulting residue by silica gel column chromatography (CHCl3/MeOH, 1:4)

Sources & evidence

ORD record
ord-7a394894f0584333ba9dec30846f3eb2
Source dataset
uspto-grants-2005_07
Patent number
US06914058B2

Reaction notes

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