Triethylamine → Ethyl 2-(3-chloro-4-methoxybenzamido)-5-phenoxybenzoate

HRID 2099974

반응식

HRID 2099974 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH:19][C:20]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:7]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1699823-Chloro-p-anisic acidHCID 57796887Ethyl 2-amino-5-phenoxybenzoate

생성물 1

HCID 57796890Ethyl 2-(3-chloro-4-methoxybenzamido)-5-phenoxybenzoate수율 95%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매3회

실험 절차

A solution of 3-chloro-4-methoxy benzoic acid (Lancaster Synthesis Ltd., Windham, N.H.) (100 mg, 0.54 mmol) in CH2Cl2 (5 mL) was cooled to −40° C. DMF (one drop) was added followed by oxalyl chloride (0.32 mL, 0.64 mmol, and 2M solution in CH2Cl2). The reaction was warmed to room temperature and stirred for 1 hour. The mixture was then concentrated to dryness and dried under high vacuum for several hours. The crude acid chloride (38 mg, 0.18 mmol) was dissolved in CH2Cl2 (2 mL) and treated with a solution of 43B (48 mg, 0.18 mmol) in CH2Cl2 (2 mL). Triethylamine (0.13 mL, 0.9 mmol) was added and the reaction was stirred at room temperature until disappearance of the starting material was noted. The reaction was concentrated to dryness and purified by chromatography (SiO2, 5% EtOAc in hexanes) to afford 43C (72 mg, 95%).

후처리

  1. concentrationThe mixture was then concentrated to dryness
  2. customdried under high vacuum for several hours
  3. stirringthe reaction was stirred at room temperature until disappearance of the starting material
  4. concentrationThe reaction was concentrated to dryness
  5. custompurified by chromatography (SiO2, 5% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-a4eda0022ff041b49814ae5c57e9903c
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569725B2

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