Thionyl Chloride → 2-[[4-(4-Pyridyl)benzoyl]amino]-N-(4-methoxyphenyl)benzamide Hydrochloride

HRID 427692

반응식

HRID 427692 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O.[NH2:20][C:21]1[CH:37]=[CH:36][CH:35]=[CH:34][C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:24]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[ClH:18].[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:20][C:21]3[CH:37]=[CH:36][CH:35]=[CH:34][C:22]=3[C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)=[O:24])=[O:13])=[CH:14][CH:15]=2)=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 24386Thionyl ChlorideHCID 4788202-amino-N-(4-methoxyphenyl)benzamideHCID 15208114-(Pyridin-4-yl)benzoic acid

생성물 1

HCID 181744352-[[4-(4-Pyridyl)benzoyl]amino]-N-(4-methoxyphenyl)benzamide Hydrochloride수율 30.7%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 1140Toluene용매2회

실험 절차

To a stirring suspension of 4-(4-pyridyl)benzoic acid (0.2 g, 1 mmol) in toluene (35 mL) was added thionyl chloride (0.55 mL, 7.5 mmol) and the mixture was heated to reflux. After 1 h the solution was cooled and added to a solution of 2-amino-N-(4-methoxyphenyl)benzamide (0.176 g, 0.73 mmol) in pyridine (2 mL) and toluene (5 mL). After stirring for 48 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was separated and washed with sat. NaHCO3, brine and dried (MgSO4), filtered and concentrated to give 103 mg of brown solid which was chromatographed by RPHPLC Method B. Upon standing, a sample of the title compound (14 mg, 4%) crystalized from one of the product containing fractions.

후처리

  1. temperaturethe mixture was heated to reflux
  2. temperatureAfter 1 h the solution was cooled
  3. customthe solvent was removed in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe organic phase was separated
  6. washwashed with sat. NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-92487b1298a04a75a2327e0b76a8b884
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313122B1

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