Triethylamine → 2-(3-Pyridinyl)-1,3-thiazol-5-amine

HRID 881999

反応式

HRID 881999 の反応式
S(=O)(=O)(O)O.[NH2:6][CH2:7][C:8]#[N:9].C(N(CC)CC)C.[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](SC)=[S:24])[CH:18]=1>CO>[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[S:24][C:7]([NH2:6])=[CH:8][N:9]=2)[CH:18]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 196971Aminoacetonitrile sulfate (1:1)HCID 117450493-Pyridinecarbodithioic acid, methyl ester

生成物 1

HCID 457887112-(3-Pyridinyl)-1,3-thiazol-5-amine収率 66.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

To a dry 500 ml round bottom flask equipped with magnetic stirrer, thermometer, bleach scrubber, and addition funnel was charged 27.6 g (179 mmoles) of aminoacetonitrile bisulfate, and 200 mLs of anhydrous methanol. The solution was cooled to ˜0° C. and 24.15 g (239 mmoles) of triethyl amine was added dropwise at a rate that maintained the temperature below 10° C. After 10 minutes, 20.2 g (119 mmoles) of methyl pyridine-3-carbodithioate was added dropwise in 50 mLs of anhydrous methanol. The reaction mixture was stirred at ambient temperature for 20 hours, after which, the solvent was removed under vacuum on a rotary evaporator. The residue was poured into 500 mLs of water and extracted with methylene chloride (4×100 mLs). The combined methylene chloride extracts were washed with 100 mLs of water, 100 mLs of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum on a rotary evaporator. The crude product was suspended in 100 mLs of ethyl ether, and the resulting yellow solid was collected by vacuum filtration to afford 14.1 g (66%) of a pale yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.97 (d, J=2.2 Hz, 1H), 8.53 (dd, J=4.8, 1.6 Hz, 1H), 8.12-8.03 (m, 1H), 7.45 (dd, J=7.9, 4.8 Hz, 1H), 6.99 (s, 1H), 6.28 (bs, 2H); 13C-NMR (101 MHz, CDCl3) δ 151.72, 148.55, 146.06, 145.40, 131.57, 130.18, 129.93, 122.20.

後処理

  1. customTo a dry 500 ml round bottom flask equipped with magnetic stirrer
  2. additionthermometer, bleach scrubber, and addition funnel
  3. temperaturemaintained the temperature below 10° C
  4. customafter which, the solvent was removed under vacuum on a rotary evaporator
  5. additionThe residue was poured into 500 mLs of water
  6. extractionextracted with methylene chloride (4×100 mLs)
  7. washThe combined methylene chloride extracts were washed with 100 mLs of water, 100 mLs of saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum on a rotary evaporator
  11. filtrationthe resulting yellow solid was collected by vacuum filtration

出典と根拠

ORDレコード
ord-1c44a246b0144da6b7da3c959a95f355
出典データセット
uspto-grants-2015_03
特許番号
US08993769B2

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