Methylamine → HCID 19987314, compound

HRID 973961Notes

Reaction equation

HRID 973961 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19]C)=O)[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH3:21][NH2:22]>C(O)C.CO>[CH3:21][NH:22][C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[C:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH:6]=1)=[O:19]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 14973214HCID 14973214, compound

Product 1

HCID 19987314HCID 19987314, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of the product of stage (i) (0.5 g) in a mixture of methylamine in ethanol (40%, 20 ml) and methanol (10 ml) was heated at reflux for 10 h. The mixture was cooled, and partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous phase was separated, and extracted with ethyl acetate (50 ml). The organic layers were combined, dried and evaporated in vacuo to give a solid, (0.25 g) which was crystallized twice from ethyl acetate to give the title compound as microcrystals (0.1 g), m.p. 125°-135°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 h
  3. temperatureThe mixture was cooled
  4. custompartitioned between water (100 ml) and ethyl acetate (100 ml)
  5. customThe aqueous phase was separated
  6. extractionextracted with ethyl acetate (50 ml)
  7. customdried
  8. customevaporated in vacuo
  9. customto give a solid, (0.25 g) which
  10. customwas crystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-cd62d2f6bd6b4973aafab12f3fcdc1d4
Source dataset
uspto-grants-1991_11
Patent number
US05066660

Reaction notes

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