Water → HCID 46945368, compound

HRID 2370597Notes

Reaction equation

HRID 2370597 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([CH3:15])([CH3:14])[N:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])[C:9]2=[O:36])=[CH:4][C:3]=1[CH3:37].[CH:38]([N:42]=[C:43]=[O:44])([CH2:40][CH3:41])[CH3:39].O>ClCCCl>[CH3:14][C:11]1([CH3:15])[C:12](=[O:13])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:43]([NH:42][CH:38]([CH3:39])[CH2:40][CH3:41])=[O:44])=[C:3]([CH3:37])[CH:4]=2)[C:9](=[O:36])[N:10]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27][CH2:28][C:29]([F:35])([F:34])[C:30]([F:33])([F:31])[F:32]

Participants

5

Reactant 3

HCID 962WaterHCID 5508502-IsocyanatobutaneHCID 46945366HCID 46945366, compound

Product 1

HCID 46945368HCID 46945368, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The compound of Example 25 (395 mg, 0.72 mmole) is dissolved in anhydrous 1,2-dichloroethane (10 ml) under an argon atmosphere, before the dropwise addition of sec-butylisocyanate (0.35 ml, 3 mmoles) at 23° C. The mixture is then heated under reflux for 24 hours. The reaction medium is then poured onto cold water and extracted using CH2Cl2. After decantation, the organic phase is washed with water and salt water. The organic solution is then dried over MgSO4, filtered, concentrated to dryness under vacuum and the evaporation residue is purified on a silica column (eluent: heptane/AcOEt: 1/0 to 4/6). The expected compound is obtained in the form of a colourless oil with a yield of 36%.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 24 hours
  3. extractionextracted
  4. washAfter decantation, the organic phase is washed with water and salt water
  5. dry with materialThe organic solution is then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under vacuum
  8. customthe evaporation residue is purified on a silica column (eluent: heptane/AcOEt: 1/0 to 4/6)

Sources & evidence

ORD record
ord-618c4242463042b18fcf5676750282e1
Source dataset
uspto-grants-2014_04
Patent number
US08710091B2

Reaction notes

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