1,2-Dichloro-3-isocyanatobenzene → N-(4-tert-butylpyridyl)-N'-(2,3-dichlorophenyl)urea

HRID 2222316Notes

Reaction equation

HRID 2222316 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[N:20]=[C:21]=[O:22]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:21]([NH:20][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=2[Cl:12])=[O:22])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 123519414-(tert-Butyl)pyridin-2-amine

Product 1

HCID 9967659N-(4-tert-butylpyridyl)-N'-(2,3-dichlorophenyl)ureaYield 91.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-amino-4-tert-butylpyridine (192 mg) and 2,3-dichlorophenyl isocyanate (240 mg) in anh. toluene (15 mL) was heated at 70° C. under argon for 24 h. The resulting mixture was diluted with EtOAc (200 mL) then washed with water (125 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to give a gum. Trituration of the gum with hexanes afforded N-(4-tert-butylpyridyl)-N′-(2,3-dichlorophenyl) urea as a white solid (394 mg, 91%): TLC (2:1 hexanes/ethyl acetate) Rf 0.40; FAB-MS m/z 338 ((M+H)+). B2a. Reaction of a Heterocyclic Amine with N,N′-Carbonyldiimidazole Followed By Reaction with a Substituted Aniline

Workup

  1. washthen washed with water (125 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a gum

Sources & evidence

ORD record
ord-4778195821734c868f2f043f6dabd051
Source dataset
uspto-grants-2008_05
Patent number
US07371763B2

Reaction notes

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