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Triethylamine → 5-Methyl-thiophene-2-carboxylic acid (5-methoxy-7-phenyl-benzothiazol-2-yl)-amide

HRID 2250698
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HRID 2250698 반응식
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][C:8]([O:17][CH3:18])=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[CH3:26][C:27]1[S:31][C:30]([C:32](Cl)=[O:33])=[CH:29][CH:28]=1.[OH-].[Na+]>ClCCl>[CH3:18][O:17][C:8]1[CH:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]2[S:3][C:2]([NH:1][C:32]([C:30]3[S:31][C:27]([CH3:26])=[CH:28][CH:29]=3)=[O:33])=[N:6][C:5]=2[CH:7]=1
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27600835-Methylthiophene-2-carbonyl chloride2회HCID 222831342-Amino-5-methoxy-7-phenylbenzothiazol

생성물 1

HCID 865849155-Methyl-thiophene-2-carboxylic acid (5-methoxy-7-phenyl-benzothiazol-2-yl)-amide수율 14.6%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

2-Amino-5-methoxy-7-phenyl-benzothiazol (45 mg, 0.18 mmol) is dissolved in dichloromethane (2 ml) and subsequently treated with triethylamine (0.073 ml, 0.53 mmol) and 5-methyl-thiophene-2-carbonyl chloride (56 mg, 0.35 mmol). After 6 h, further 0.073 ml, 0.53 mmol) and 5-methyl-thiophene-2-carbonyl chloride (56 mg, 0.35 mmol) are added and the mixture is stirred for additional 18 h at ambient. After addition of 0.1M aqueous sodium hydroxide, the mixture is stirred for additional 16 h. The organic layer is separated, dried and evaporated to dryness. Flash chromatography (silica, eluent ethyl acetate/cyclohexane 1:1, containing 0.5% of 25% aqueous ammonia) affords (10 mg, 5%) of the product as white solid. MS: m/e=380 (M+).

후처리

  1. stirringthe mixture is stirred for additional 16 h
  2. customThe organic layer is separated
  3. customdried
  4. customevaporated to dryness
  5. additionFlash chromatography (silica, eluent ethyl acetate/cyclohexane 1:1, containing 0.5% of 25% aqueous ammonia)

출처 및 근거

ORD 기록
ord-cfda860892784cd19e647812a1559a00
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07317007B2

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