Aniline → HCID 14369791, compound

HRID 1381894Notes

Reaction equation

HRID 1381894 reaction equation
C([Li])CCC.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:13][C:14]1[N:15]=[C:16]([C:25](OC)=[O:26])[S:17][C:18]=1[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>O1CCCC1>[CH3:13][C:14]1[N:15]=[C:16]([C:25]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:26])[S:17][C:18]=1[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 14369785HCID 14369785, compoundHCID 178418339Butyllithium

Product 1

HCID 14369791HCID 14369791, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (14-17% in hexane, 1.2ml) was added to dropwise a stirred solution of aniline (0.12 ml) in dry tetrahydrofuran (3 ml) at room temperature under nitrogen atmosphere. Then, methyl 4-methyl-5-(4-pyridinyl)-thiazole-2-carboxylate (200 mg) was added to a stirred solution at room temperature under nitrogen atmosphere, and the mixture was stirred in the same condition for 1 hour. The resulting precipitates were collected by filtration, and the precipitates were washed with water, and air-dried. The precipitate was recrystallized from benzenepetroleum ether to give 4-methyl-5-(4-pyridinyl)-thiazole-2-carboxanilide (80 mg, yield 33.3%) as colorless plates.

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washthe precipitates were washed with water
  4. customair-dried
  5. customThe precipitate was recrystallized from benzenepetroleum ether

Sources & evidence

ORD record
ord-9ea7c5382b3c454d90851d52be82a9ba
Source dataset
uspto-grants-1989_02
Patent number
US04804668

Reaction notes

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