Ethyl isocyanate → HCID 68839047, compound

HRID 2112970Notes

Reaction equation

HRID 2112970 reaction equation
[CH3:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]2[N:13]3[N:14]=[C:15]([NH2:17])[N:16]=[C:12]3[CH:11]=[C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:9]=2)=[CH:4][N:3]=1.[CH2:24]([N:26]=[C:27]=[O:28])[CH3:25].CO.C(Cl)(Cl)Cl>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.C1COCC1.C1(C)C=CC=CC=1>[CH3:7][N:6]1[C:5]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:27]([NH:26][CH2:24][CH3:25])=[O:28])[N:16]=[C:12]3[CH:11]=[C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:9]=2)=[CH:4][N:3]=[C:2]1[CH3:1]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 21584188Chloroform methanolHCID 68837044HCID 68837044, compound

Product 1

HCID 68839047HCID 68839047, compound

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the product of Step 1 (0.37 g, 1.21 mmol), ethylisocyanate (0.43 g, 6.05 mmol) and a catalytic quantity of dibutyltin diacetate (5 drops) in THF/toluene (1:1, 10 mL) was heated in a sealed tube at 100° C. for 15 h. This mixture was cooled to 0° C., the solid obtained was filtered and washed with 10% CHCl3/hexanes to isolate crude product. The solid was taken up into MeOH/CHCl3, and dried onto silica gel. This material was then purified by column chromatography on silica gel (1-8% MeOH/CHCl3 as eluant) followed by trituration with chloroform (10 mL) and hexanes (500 mL) to isolate the title compound as a solid. LCMS (APCI+) 377.

Workup

  1. customthe solid obtained
  2. filtrationwas filtered
  3. washwashed with 10% CHCl3/hexanes
  4. customto isolate crude product
  5. customdried onto silica gel
  6. customThis material was then purified by column chromatography on silica gel (1-8% MeOH/CHCl3 as eluant)

Sources & evidence

ORD record
ord-d09c80c8147e4ea6bcccc17c6eb062e1
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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