Benzyl isocyanate → HCID 18700037, compound

HRID 2288606Notes

Reaction equation

HRID 2288606 reaction equation
[CH2:1]([N:8]=[C:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][C:12]1[NH:16][N:15]=[C:14]([C:17]2[S:21][C:20]([CH2:22][N:23]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[N:13]=1>CN(C)C=O>[NH2:11][C:12]1[N:16]([C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[N:15]=[C:14]([C:17]2[S:21][C:20]([CH2:22][N:23]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[N:13]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 178508296HCID 178508296, compound

Product 1

HCID 18700037HCID 18700037, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5 ml of N,N-dimethylformamide solution containing 331 mg (2.49 mmol) of benzyl isocyanate was added to 75 ml of N,N-dimethylformamide solution containing 690 mg (2.49 mmol) of the compound of Example 38, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated, 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 (75:1) to give 1.07 g of the title compound. This was crystallized by adding an appropriate amount of diethyl ether and then recrystallized from ethyl acetate-n-hexane to give 564 mg of the compound of interest.

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe resulting residue was dissolved in chloroform
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. washwas eluted with chloroform-methanol (75:1)

Sources & evidence

ORD record
ord-9e6ab84d88bb42d0a05ac8b4b65cc3bc
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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