Benzyl isocyanate → HCID 18700048, compound

HRID 2288603Notes

Reaction equation

HRID 2288603 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[N:9]=[C:8]([C:10]2[S:14][C:13]([CH2:15][N:16]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[O:7][N:6]=1.[CH2:23]([N:30]=[C:31]=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([NH:30][C:31]([NH:3][CH2:4][C:5]1[N:9]=[C:8]([C:10]2[S:14][C:13]([CH2:15][N:16]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[O:7][N:6]=1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 18700052HCID 18700052, compound

Product 1

HCID 18700048HCID 18700048, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

770 mg (2.63 mmol) of the free form compound obtained in Example 8 was dissolved in 20 ml of DMF, and 5 ml of DMF solution containing 369 mg (2.77 mmol) of benzyl isocyanate was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under a reduced pressure, and the resulting residue was dissolved in chloroform, washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the resulting residue was subjected to a silica gel column chromatography, which was eluted with chloroform-methanol (50:1) to give 1.0 g of the title compound.

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under a reduced pressure
  3. dissolutionthe resulting residue was dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. washwas eluted with chloroform-methanol (50:1)

Sources & evidence

ORD record
ord-fe886f1dd937442a93c968a9bc988d2b
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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