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

HRID 2099974

反応式

HRID 2099974 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒3 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-a4eda0022ff041b49814ae5c57e9903c
出典データセット
uspto-grants-2009_08
特許番号
US07569725B2

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