Triethylamine → Benzanilide

HRID 1017808

반응식

HRID 1017808 반응식
C(OC)(=O)[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[CH:36]=[CH:35][C:24](C(OCC2C=CC=CC=2)=O)=[CH:23][CH:22]=1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C=O)C.C(Cl)Cl>[C:6]([NH:20][C:21]1[CH:36]=[CH:35][CH:24]=[CH:23][CH:22]=1)(=[O:8])[C:5]1[CH:4]=[CH:3][CH:2]=[CH:10][CH:9]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 98488Benzyl p-aminobenzoateHCID 36144541,4-Benzenedicarboxylic acid, methyl ester

생성물 1

HCID 7168Benzanilide수율 134.8%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of mono-methyl terephthalate (4.00 g, 22 mmol) in ethyl acetate (25 mL) and DMF (0.1 mL) was cooled in an ice bath and treated with oxalyl chloride (11 mL, 2N in CH2Cl2, 22 mmol) over 30 minutes. After stirring 2 hours at room temperature the solvent was removed on a rotary evaporator and the residue dissolved in CH2Cl2 (20 mL) and added to a solution of benzyl 4-aminobenzoate (5.00 g, 22 mmol) in CH2Cl2 (25 mL) and triethylamine (4.3 mL, 31 mmol) at −60° C. The reaction mixture was warmed to room temperature for 1 hour and then partitioned between water and ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, filtered, and evaporated. The residue was recrystallized from t-butyl methyl ether to give 5.85 g of compound 8.

후처리

  1. customwas removed on a rotary evaporator
  2. dissolutionthe residue dissolved in CH2Cl2 (20 mL)
  3. temperatureThe reaction mixture was warmed to room temperature for 1 hour
  4. custompartitioned between water and ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was recrystallized from t-butyl methyl ether

출처 및 근거

ORD 기록
ord-9f8d21a2aa104ff597679c335e1f7e44
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479548B2

연결된 노트

불러오는 중…