Water → HCID 14648416, compound

HRID 613165Notes

Reaction equation

HRID 613165 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 chromatography 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-9e930e9685b4439b81c688aac60cb46a
Source dataset
uspto-grants-1999_12
Patent number
USRE036477

Reaction notes

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