3,5-Dichlorophenyl isocyanate → HCID 178522179, compound

HRID 2262765Notes

Reaction equation

HRID 2262765 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)[CH:3]=1.[Cl:14][C:15]1[CH:16]=[C:17]([N:22]=[C:23]=[O:24])[CH:18]=[C:19]([Cl:21])[CH:20]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:23]([NH:22][C:17]2[CH:18]=[C:19]([Cl:21])[CH:20]=[C:15]([Cl:14])[CH:16]=2)=[O:24])=[C:4]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 178507588HCID 178507588, compound

Product 1

HCID 178522179HCID 178522179, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-2-(1H-tetrazol-5-yl)-phenylamine (500 mg) dissolved in toluene (15 ml) was treated with 3,5-dichlorophenylisocyanate (500 mg) and stirred for a week. The precipitated product was filtered, washed with toluene, dissolved in acetone, filtered through celite, precipitated again with water, filtered and dried. This residue was slurried in 96% EtOH, and adjusted to basic pH with 10 N NaOH. The solution was filtered through celite and re-acidified with 4N HCl and a little water. The precipitated product was filtered and washed with water to afford 1-[4-Chloro-2-(1H-tetrazol-5-yl)-phenyl]-3-(3,5-dichloro-phenyl)-urea as a white solid (720 mg ). Mp.=234-236° C.

Workup

  1. filtrationThe precipitated product was filtered
  2. washwashed with toluene
  3. dissolutiondissolved in acetone
  4. filtrationfiltered through celite
  5. customprecipitated again with water
  6. filtrationfiltered
  7. customdried
  8. filtrationThe solution was filtered through celite and re-acidified with 4N HCl
  9. filtrationThe precipitated product was filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-fa6a7d77323f447b8caee6cb77acc05a
Source dataset
uspto-grants-2010_12
Patent number
US07851492B2

Reaction notes

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