Triethylamine → HCID 18756251, 화합물

HRID 434060노트

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HRID 434060 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[N+:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])#[C-:19].CCN(CC)CC>CN(C=O)C.C1COCC1.C(Cl)Cl>[CH3:24][O:23][C:21]([C:20]1[N:18]=[CH:19][O:6][C:4]=1[C:3]1[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])=[O:22]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 679472-Chloro-6-fluorobenzoic acidHCID 547815Methyl isocyanoacetate

생성물 1

HCID 18756251HCID 18756251, 화합물수율 24%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-chloro-6-fluorobenzoic acid (2.14 g, 12.3 mmol), CH2Cl2 (50 ml), and DMF (2 drops) at room temperature under N2 was added oxalyl chloride (9.2 ml, 18.4 mmol) dropwise. The mixture was stirred for 3 h and the volatiles were removed under reduced pressure to give the crude acid chloride. The crude acid chloride and methyl isocyanoacetate (1.23 g, 12.3 mmol) were dissolved in THF (20 ml) at room temperature under N2 and Et3N (6.8 ml, 49.2 mmol) was added dropwise over a period of 30 minutes. The reaction was allowed to stir for 22 h followed by dilution with Et2O, extraction with H2O, 1N HCl, H2O, brine, dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexanes/Et2O gradient) gave 4-methoxycarbonyl-5-(2-chloro-6-fluorophenyl)oxazole (0.74 g, 24%).

후처리

  1. customthe volatiles were removed under reduced pressure
  2. customto give the crude acid chloride
  3. stirringto stir for 22 h
  4. extractionfollowed by dilution with Et2O, extraction with H2O, 1N HCl, H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e7c26230571848e4a0c799777005a8f7
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06670373B1

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