Dimethyl Sulfoxide → HCID 178511885, compound

HRID 369978Notes

Reaction equation

HRID 369978 reaction equation
Cl.Cl.[CH2:3]1[CH:16]2[N:7]([CH2:8][C:9]3[CH:10]=[C:11]([NH2:17])[CH:12]=[CH:13][C:14]=3[CH2:15]2)[CH2:6][CH2:5][O:4]1.C[S:19](C)=O.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[CH2:3]1[CH:16]2[N:7]([CH2:8][C:9]3[CH:10]=[C:11]([NH:17][C:23]([C:24]4[S:19][CH:27]=[CH:26][CH:25]=4)=[NH:22])[CH:12]=[CH:13][C:14]=3[CH2:15]2)[CH2:6][CH2:5][O:4]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 21584261HCID 21584261, compound

Product 1

HCID 178511885HCID 178511885, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of 3,4,5,6,11,11a-hexahydro-1H-[1,4]oxazino[4,3-b]isoquinolin-8-amine dihydrochloride (0.461 g, 1.66 mmol) and methyl sulfoxide (5 ml) was added pyridine (0.28 ml) followed by S-methyl-2-thiophenethiocarboximide hydroiodide (0.612 g). The mixture was heated at 50° C., with stirring, for 4 h. The reaction mixture was then poured into water (50 ml) and after stirring for 1 hour, the mixture was clarified by filtration. The filtrate was basified with concentrated ammonium hydroxide to precipitate the product as a solid. The product was isolated, washed with water and dried; yield 0.4917 g, m.p. 190-4° C., MS 314 (M+H)+.

Workup

  1. stirringafter stirring for 1 hour
  2. filtrationthe mixture was clarified by filtration
  3. customto precipitate the product as a solid
  4. customThe product was isolated
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b141f6238b194f92bf20ae30cc5d6eb6
Source dataset
uspto-grants-2000_10
Patent number
US06140322

Reaction notes

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