Cyanamide → HCID 68880653, compound

HRID 1723658Notes

Reaction equation

HRID 1723658 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:13]#CN.[CH2:16]([N:23]1[C:27]([C:28](=O)[CH:29]=[CH:30][N:31](C)[CH3:32])=[CH:26][N:25]=[C:24]1[CH3:35])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[O-].[Na+]>CO.Cl.CC(N(C)C)=O>[CH2:16]([N:23]1[C:27]([C:28]2[CH:29]=[CH:30][N:31]=[C:32]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[NH:11][CH3:12])=[CH:4][CH:3]=3)[N:13]=2)=[CH:26][N:25]=[C:24]1[CH3:35])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 9864CyanamideHCID 743684-amino-N-methylbenzene-1-sulfonamideHCID 10942334Sodium MethoxideHCID 68883764HCID 68883764, compound

Product 1

HCID 68880653HCID 68880653, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Amino-N-methyl-benzenesulphonamide (250 mg, 1.34 mmol) was dissolved in the minimum amount of MeOH and 1M ethereal hydrogen chloride (1.34 ml) added. The volatiles were removed by evaporation and cyanamide (68 mg, 1.62 mmol) was added followed by dimethylacetamide (0.5 ml) and the mixture heated at 100° C. for 45 minutes. The mixture was allowed to cool and 1-benzyl-5-(3-dimethylaminoprop-2-en-1-oyl)-2-methylimidazole (Method 50; 230 mg, 0.86 mmol) and sodium methoxide (150 mg, 2.78 mmol) were added and the mixture heated to reflux for one hour. The mixture allowed to cool and was partitioned between EtOAc and aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried (Na2SO4) and the volatiles removed by evaporation. The residue was purified by chromatography on silica eluting with DCM/7N methanolic ammonia (96:4). The purified product was triturated with minimal hot EtOAc to give the title compound (260 mg, 70%) as a cream solid. NMR: 2.28 (s, 3H), 2.37 (d, 3H), 5.96 (s, 2H), 6.93 (d, 2H), 7.15-7.28 (m, 5H), 7.54 (d, 2H), 7.75-7.81 (m, 3H), 8.40 (d, 1H), 9.86 (s, 1H); m/z 435.

Workup

  1. additionadded
  2. additionwas added
  3. temperatureto cool
  4. temperaturethe mixture heated
  5. temperatureto reflux for one hour
  6. temperatureto cool
  7. customwas partitioned between EtOAc and aqueous sodium hydrogen carbonate solution
  8. customThe organic layer was separated
  9. washwashed with brine
  10. dry with materialdried (Na2SO4)
  11. customthe volatiles removed by evaporation
  12. customThe residue was purified by chromatography on silica eluting with DCM/7N methanolic ammonia (96:4)
  13. customThe purified product was triturated with minimal hot EtOAc

Sources & evidence

ORD record
ord-9ac595a0e5a047b6ac9efad9cb3d2f3e
Source dataset
uspto-grants-2009_02
Patent number
US07485638B2

Reaction notes

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