Carbon Dioxide → Vitalethine

HRID 430416Notes

Reaction equation

HRID 430416 reaction equation
[CH2:1]([C:4]([NH:6][CH2:7][CH2:8][S:9][S:10][CH2:11][CH2:12][NH:13][C:14]([CH2:16][CH2:17][NH2:18])=[O:15])=[O:5])[CH2:2][NH2:3].[OH-:19].[Na+].[C:21](Cl)(Cl)=[O:22].N#N.[C:27](=[O:29])=[O:28]>N1C=CC=CC=1.CS(C)=O>[CH2:1]([C:4]([NH:6][CH2:7][CH2:8][S:9][S:10][CH2:11][CH2:12][NH:13][C:14]([CH2:16][CH2:17][NH:18][C:21]([OH:22])=[O:19])=[O:15])=[O:5])[CH2:2][NH:3][C:27]([OH:29])=[O:28]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 947NitrogenHCID 6371Phosgene2×HCID 14798Sodium HydroxideHCID 69532Alethine

Product 1

HCID 197482Vitalethine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolvent

Procedure

To a suspension of ZnO (6.5 mg from King's Specialty Company, Fort Wayne, Ind., U.S.A.) and β-alethine (6.35 mg from Example IV. A. above) in pyridine (12.6 mg from Fisher Scientific, Fair Lawn, N.J., U.S.A.) and dimethylsulfoxide (0.5 ml from Sigma Chemical Company, St. Louis, Mo., U.S.A.), and in a vessel equipped with a gas trap containing sodium hydroxide (at least 1M), was added 0.2 ml of a solution of phosgene (20% in toluene from Fluka Chemical Corp, Ronkonkoma, N.Y., USA). Packing of the reaction vessel in dry ice controls the exothermic reaction and improves yields of large-scale preparations. After 48 hours of reaction the excess phosgene was blown into the alkali trap with N2. The product was precipitated in the vessel with acetonitrile (approximately 50 mls from Fisher Scientific, Fair Lawn, N.J., U.S.A.). Vitalethine can be recrystallized from water with acetonitrile.

Workup

  1. customthe exothermic reaction
  2. customimproves yields of large-scale preparations
  3. customThe product was precipitated in the vessel with acetonitrile (approximately 50 mls from Fisher Scientific, Fair Lawn, N.J., U.S.A.)
  4. customVitalethine can be recrystallized from water with acetonitrile

Sources & evidence

ORD record
ord-1ca9aaf8749248e3a961a9a7a3d34a06
Source dataset
uspto-grants-2001_11
Patent number
US06323025B1

Reaction notes

Loading…