Methanol → N-(((4-((5-Bromo-2-pyrimidinyl)oxy)-3-chlorophenyl)amino)carbonyl)-2-nitrobenzamide

HRID 4513Notes

Reaction equation

HRID 4513 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[Cl:16])=[N:6][CH:7]=1.[N+:17]([C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[C:22]([N:24]=[C:25]=[O:26])=[O:23])([O-:19])=[O:18].O.CO>O1CCOCC1>[N+:17]([C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[C:22]([NH:24][C:25]([NH:13][C:12]1[CH:14]=[CH:15][C:9]([O:8][C:5]2[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[C:10]([Cl:16])[CH:11]=1)=[O:26])=[O:23])([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 125834382-Nitrobenzoyl isocyanateHCID 137714404-(5-Bromo-2-pyrimidinyloxy)-3-chloroaniline

Product 1

HCID 128803N-(((4-((5-Bromo-2-pyrimidinyl)oxy)-3-chlorophenyl)amino)carbonyl)-2-nitrobenzamideYield 84.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Into a flask, a solution obtained by dissolving 6.80 g of the above 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline in 30 ml of dioxane, was introduced, and a solution obtained by dissolving 5.76 g of 2-nitrobenzoylisocyanate in 30 ml of dioxane, was dropwise added thereto, and then the mixture was reacted at room temperature for 9 hours. After the completion of the reaction, the product was poured into water, subjected to filtration and washed with hot water. The crystals thereby obtained were put into methanol, and stirred, and then subjected to filtration again, to obtain 9.42 g of the desired product having a melting point of from 234 to 236° C.

Workup

  1. customInto a flask, a solution obtained
  2. additionwas introduced
  3. customa solution obtained
  4. additionwas dropwise added
  5. customthe mixture was reacted at room temperature for 9 hours
  6. customAfter the completion of the reaction
  7. filtrationsubjected to filtration
  8. washwashed with hot water
  9. customThe crystals thereby obtained
  10. filtrationsubjected to filtration again

Sources & evidence

ORD record
ord-5d8975024a1740ce98c9290e59b3aec3
Source dataset
uspto-grants-1988_02
Patent number
US04727077

Reaction notes

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