Benzene, 1-chloro-3-isocyanato- → HCID 9890963, compound

HRID 377792Notes

Reaction equation

HRID 377792 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:12]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[Cl:24][C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1>CN(C=O)C>[ClH:24].[Cl:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]([N:14]([CH2:13][C:12]2[N:8]([CH2:7][C:6]3[CH:20]=[CH:21][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[CH:9]=[N:10][CH:11]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:33])[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 24758Sodium hydrideHCID 19357217HCID 19357217, compound

Product 1

HCID 9890963HCID 9890963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the amine 7 (prepared above) in 2 mL of dry DMF at 0° C. was added NaH (37 mg, 60% dispersion in mineral oil). The solution was warmed to room temperature for 10 minutes, then recooled to 0° C. 3-Chlorophenylisocyanate (0.084 mL) was added dropwise, and the cooling bath was removed. After three hours, the reaction was poured into EtOAc/hexane (2:1) and water, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude urea 1 as a yellow foam. Half of this material was purified by silica gel chromatography (3-5% MeOH/CH2Cl2), taken up in CH2Cl2 and treated with 1 M HCl/ether solution, and concentrated in vacuo. The product hydrochloride 1 (75 mg) was isolated as a yellow solid.

Workup

  1. customrecooled to 0° C
  2. customthe cooling bath was removed
  3. additionthe reaction was poured into EtOAc/hexane (2:1) and water
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide the crude urea 1 as a yellow foam
  9. customHalf of this material was purified by silica gel chromatography (3-5% MeOH/CH2Cl2)
  10. additiontreated with 1 M HCl/ether solution
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a1c430a1fd44367b96895dc3ddaa981
Source dataset
uspto-grants-2000_02
Patent number
US06028201

Reaction notes

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