Phenyl isocyanate → HCID 21946003, compound

HRID 2216985Notes

Reaction equation

HRID 2216985 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][CH:11]([C:13]1[C:14](Cl)=[N:15][C:16]([Cl:19])=[N:17][CH:18]=1)[CH3:12].[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[N-]=C=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N:10]([CH:11]([C:13]1[CH:14]=[N:15][C:16]([Cl:19])=[N:17][CH:18]=1)[CH3:12])[C:28]([NH:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:29]

Participants

4

Reactant 3

HCID 7672Phenyl isocyanateHCID 105034IsocyanateHCID 10426913HCID 10426913, compound

Product 1

HCID 21946003HCID 21946003, compound

Conditions

Temperature
150 °C

Procedure

(±)-(2-Chloro-5-methoxy-phenyl)-[1-(2,4-dichloro-pyrimidin-5-yl)-ethyl]-amine (70 mg; 0.21 mmol) (from Example 12a supra) was combined with phenyl isocyanate (60 μL; 0.55 mmol) (Aldrich) and heated (neat) at 150° C. for 65 minutes. Thin layer chromatography analysis showed some unreacted starting material remained. Additional isocyanate (20 μL; 0.18 mmol) was added and the mixture heated at 150° C. for an additional 30 minutes. Upon cooling, hexanes was added. After stirring, the supernatant was decanted off and the residue dried to give the intermediate (±)-1-(2-chloro-5-methoxy-phenyl)-1-[1-(2-chloropyrimidin-5-yl)-ethyl]-3-phenyl-urea which contained about 20% starting material by HPLC.

Workup

  1. temperaturethe mixture heated at 150° C. for an additional 30 minutes
  2. temperatureUpon cooling
  3. customthe supernatant was decanted off
  4. customthe residue dried

Sources & evidence

ORD record
ord-84c5c0f7f8b64f5a8c76a8abd240abdc
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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