Hydrochloric Acid → 2-Chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-N'-methylbenzenesulfonimidamide

HRID 247002Notes

Reaction equation

HRID 247002 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](=[N:11][CH3:12])([NH2:10])=[O:9].C1(O[C:20](=[O:31])[NH:21][C:22]2[N:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([CH3:30])[N:23]=2)C=CC=CC=1.N12CCCN=C1CCCCC2.Cl>C(#N)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](=[N:11][CH3:12])([NH:10][C:20]([NH:21][C:22]1[N:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([CH3:30])[N:23]=1)=[O:31])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11448329Carbamic acid, (4-methoxy-6-methyl-1,3,5-triazin-2-yl)-, phenyl esterHCID 201610532-chloro-N'-methylbenzenesulfonimidamide

Product 1

HCID 139209102-Chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-N'-methylbenzenesulfonimidamideYield 22.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 196.8 mg (0.96 mmol) of 2-chloro-N'-methylbenzenesulfonimidamide and 250 mg (0.96 mmol) of phenyl(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate in 5 mL of dry acetonitrile was added 0.15 mL (1.0 mmol) of 1,8-diazabicyclo[5.4.0]-undec-7-ene. After 45 minutes at room temperature, 5 mL of water and 2.5 mL of 5% HCl were added. The aqueous layer was extracted with methylene chloride (3×10 mL). The organic layer was dried (Na2SO4), filtered and the solvent was removed with a rotary evaporator. The residue was triturated with ethyl acetate to give 80 mg of a white solid; m.p. 154° to 160° C.

Workup

  1. extractionThe aqueous layer was extracted with methylene chloride (3×10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was removed with a rotary evaporator
  5. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-2bb6864443d34946aafac4f23f3ec10e
Source dataset
uspto-grants-1987_11
Patent number
US04705555

Reaction notes

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