1-Methylthio-1-methylamino-2-nitroethylene → HCID 70449601, compound

HRID 1589544Notes

Reaction equation

HRID 1589544 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]=[C:8]([NH:10][CH2:11][CH:12]([OH:28])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:16]=2)[N:7]([CH3:29])[N:6]=1.[CH3:30][NH:31][C:32](SC)=[CH:33][N+:34]([O-:36])=[O:35]>O.CO.C(OCC)(=O)C>[CH3:29][N:7]1[C:8]([NH:10][CH2:11][CH:12]([OH:28])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:16]=2)=[N:9][C:5]([CH2:4][CH2:3][CH2:2][NH:1][C:32]([NH:31][CH3:30])=[CH:33][N+:34]([O-:36])=[O:35])=[N:6]1

Participants

6

Reactant 2

HCID 1235491-Methylthio-1-methylamino-2-nitroethylene2×HCID 20246012HCID 20246012, compound

Product 1

HCID 70449601HCID 70449601, compoundYield 38.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-[[3-(3-aminopropyl)-1-methyl-1H-1,2,4-triazol-5-yl]amino]-3-[3-(1-piperidinylmethyl)phenoxy]-2-propanol (0.25 g) and N-methyl-1-(methylthio)-2-nitroethenamine (0.1 g) in water (6 ml) and methanol (6 ml) was stirred at room temperature for 24 h. A further quantity of N-methyl-1-(methylthio)-2-nitroethenamine (0.01 g) was added and the mixture stirred for a further 3 h. The reaction mixture was concentrated to ca. 6 ml, diluted with water (10 ml), acidified to pH3 with acetic acid and washed with ethyl acetate. The aqueous solution was basified with excess potassium carbonate and extracted with ethyl acetate. The extract was dried and evaporated to leave a brown gum which was chromatographed on silica using methanol:ammonia (250:1) to give a gum which was dissolved in hot ethyl acetate and cooled to precipitate a gum. This gum was dissolved in chloroform and filtered through florosil and hyflo. The filtrate was evaporated to give the title compound (0.12 g) as a solid white foam m.p. 60°-63° (softens).

Workup

  1. concentrationThe reaction mixture was concentrated to ca. 6 ml
  2. additiondiluted with water (10 ml)
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. customThe extract was dried
  6. customevaporated
  7. customto leave a brown gum which
  8. customwas chromatographed on silica
  9. customto give a gum which
  10. temperaturecooled
  11. customto precipitate a gum
  12. dissolutionThis gum was dissolved in chloroform
  13. filtrationfiltered through florosil and hyflo
  14. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a2ed75a2c7b44d7d9fdd2f86bbc01231
Source dataset
uspto-grants-1986_02
Patent number
US04571394

Reaction notes

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