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Diisopropylethylamine → 3-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

HRID 1844645
ノート
印刷プレビュー

反応式

HRID 1844645 の反応式
[CH3:1][C:2]1[CH:10]=[C:9](/[C:11](/[S:18][CH3:19])=[N:12]/[CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[S:20]1[CH2:23][CH:22]([NH2:24])[CH2:21]1.CCN(C(C)C)C(C)C.F[B-](F)(F)F.BrC1C=CC=C[N+]=1CC>ClCCl.O>[CH3:19][S:18][C:11](=[N:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:9]1[CH:8]=[CH:7][C:3]([C:4](=[O:6])[NH:24][CH:22]2[CH2:23][S:20][CH2:21]2)=[C:2]([CH3:1])[CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 27363002-Bromo-1-ethylpyridinium tetrafluoroborateHCID 14594132Thietan-3-amineHCID 874255662-methyl-4-[(Z)-C-methylsulfanyl-N-(trimethylsilylmethyl)carbonimidoyl]benzoic acid

生成物 1

HCID 675060713-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester収率 12.1%

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-methyl-4-{methylsulfanyl-[(Z)-trimethylsilanyl methylimino]methyl}-benzoic acid (Example I18) (107 mg) in dichloromethane (6 ml) was added thietan-3-ylamine (88 mg), Hünigs base (0.248 ml) and 2-bromo-1-ethyl-pyridinium tetrafluoroborate (169 mg). The reaction mixture was stirred at ambient temperature for 2 hours. Water was added and the mixture was extracted twice with dichloromethane. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:3) to give 3-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (16 mg). 1H-NMR (400 MHz, CDCl3): 7.40-7.20 (m, 3H), 6.20 (d, 1H); 5.30 (m, 1H), 3.55 (s, 2H), 3.35 (m, 2H), 3.25 (m, 2H), 2.35 (s, 3H), 1.95 (s, 3H), 0.00 (s, 9H) ppm.

後処理

  1. extractionthe mixture was extracted twice with dichloromethane
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:3)

出典と根拠

ORDレコード
ord-48181dce10e04fc99b133e67073d8896
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946447B2

反応ノート

読み込み中…

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