Acetyl chloride → HCID 19900379, compound

HRID 1029394Notes

Reaction equation

HRID 1029394 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[N:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=2)=[C:12]([CH3:24])[CH:11]=1)=[O:8])=[O:5].[C:29](Cl)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([NH:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[N:22]=[CH:21][C:20]([Br:23])=[CH:19][N:18]=2)=[C:12]([CH3:24])[CH:11]=1)=[O:8])=[O:5])(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 372559HCID 372559, compound

Product 1

HCID 19900379HCID 19900379, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.3 g of N-(2-aminobenzoyl)-N'-[4-(5-bromo-2-pyrimidinyloxy)-3-methylphenyl]urea (Compound No. 27 as described hereinafter) as prepared in accordance with Preparation Example 3, was added to 30 ml of pyridine, and 0.25 ml of acetyl chloride was dropwise added thereto under cooling with ice. The mixture was stirred at room temperature for 2 hours and 30 minutes. Then, pyridine was distilled off, and the residue was purified by silica gel column chromatography (developing solvent; methylene chloride:ethyl acetate=7:3) to obtain 1.18 g of the desired product (melting point: 186°-191° C.) (Compound No. 49 as described hereinafter).

Workup

  1. customas prepared in accordance with Preparation Example 3
  2. additionwas dropwise added
  3. temperatureunder cooling with ice
  4. distillationThen, pyridine was distilled off
  5. customthe residue was purified by silica gel column chromatography (developing solvent; methylene chloride:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-581a664841be4ec99af15a79c5ecc338
Source dataset
uspto-grants-1992_04
Patent number
US05102884

Reaction notes

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