1-Butanol → HCID 21923048, compound

HRID 1244932Notes

Reaction equation

HRID 1244932 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:14])[CH2:12][CH3:13])=[C:4](Cl)[N:3]=1.C(O)CCC.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:14])[CH2:12][CH3:13])=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 6115AnilineHCID 21922929HCID 21922929, compound

Product 1

HCID 21923048HCID 21923048, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The operation is carried out as in Stage 2 of Example 9 starting from 200 mg of the product obtained in Stage 1 of Example 9 and 4 ml of butanol and using 0.091 ml of aniline in place of the benzylamine. Agitation is carried out at ambient temperature then the reaction medium is taken to a temperature of 80 to 85° C. for approximately 22 hours, left to return to ambient temperature, diluted with 4 ml of isopropanol and placed for two days at a temperature of approximately 0° C., followed by separating, washing with 5 ml of isopropanol and drying at a temperature of approximately 80° C. After purification on silica eluting with methylene chloride/ethyl acetate in a proportion of 90/10, 176 mg of expected product is obtained in the form of white crystals.

Workup

  1. customis carried out at ambient temperature
  2. waitleft
  3. customto return to ambient temperature
  4. waitplaced for two days at a temperature of approximately 0° C.
  5. customby separating
  6. washwashing with 5 ml of isopropanol
  7. customdrying at a temperature of approximately 80° C
  8. customAfter purification on silica eluting with methylene chloride/ethyl acetate in a proportion of 90/10

Sources & evidence

ORD record
ord-154d9e76d048470aacb16b1c8bdf2886
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

Loading…