Water → HCID 14648416, compound

HRID 466321Notes

Reaction equation

HRID 466321 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].N1C=CC=CC=1.Cl[C:19]([C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)=[O:20].O>C1C=CC=CC=1>[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[CH:4]=[C:5]([NH:6][C:19]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=2)=[O:20])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 124888833-(Trimethylsilyl)aniline

Product 1

HCID 14648416HCID 14648416, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 135 mg (0.817 mmol) of m-trimethylsilylaniline in 8 ml of dry benzene were added 1.0 ml of dry pyridine and 179 mg (0.900 mmol) of methyl p-chloroformylbenzoate, successively. The mixture was stirred at room temperature for 20 hours. To the reaction mixture was added water and the aqueous solution was extracted with AcOEt. The extract was washed successively with water, sat.eq.NaHCO3 and sat.ag.NaCl, dried and evaporated to give 272 mg of white powder, which was purified by column chlomatography on silica gel (eluent: methylene chloride) to give 266 mg of white powder (yield: 99%). Recrystallization of the powder from a mixture of methylene chloride, n-hexane and chloroform gave 120 mg of white needles, m.p. 125°-126° C. (yield 45%).

Workup

  1. extractionthe aqueous solution was extracted with AcOEt
  2. washThe extract was washed successively with water, sat.eq
  3. dry with materialNaCl, dried
  4. customevaporated

Sources & evidence

ORD record
ord-d96c46bb15104a86b842bd610362f20a
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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