Triethylamine → HCID 4444271、化合物

HRID 1066877ノート

反応式

HRID 1066877 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:12]([N:18]=[C:19]=[S:20])[CH:13]1[O:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(O)C>[Br:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:19](=[S:20])[N:18]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][O:17]1)[C:4]2=[O:6]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 798582-Amino-5-bromobenzoic acidHCID 1421082-(Isothiocyanatomethyl)oxolane

生成物 1

HCID 4444271HCID 4444271、化合物収率 90.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-amino-5-bromobenzoic acid (8.0 g, 37.0 mmol), tetrahydrofurfuryl isothiocyanate (5.0 g, 34.9 mmol) and triethylamine (5.0 mL, 3.6 g, 35.6 mmol) in ethanol (48 mL) was heated at reflux for 2 h. The reaction mixture was then allowed to cool to room temperature and filtered. The resulting filter cake was washed with 50 mL of cold ethanol, followed by 50 mL of hexanes to provide 10.8 g of the title compound of Step A as a solid melting at 230-232° C. 1H NMR (400 MHz, Me2SO-d6): δ 1.63-2.0 (m,4H), 3.58-3.68 (m,1H), 3.74-3.82 (m,1H), 4.32 (dd,1H), 4.39-4.50 (m,1H), 4.58 (dd,1H), 7.37 (d,1H), 7.91 (d,1H), 8.02 (s,1H), 13.1 (br s,1H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. filtrationThe resulting filter cake
  5. washwas washed with 50 mL of cold ethanol

出典と根拠

ORDレコード
ord-d76630f41cc54cc8a598d8c3f572cf35
出典データセット
uspto-grants-2001_06
特許番号
US06245770B1

反応ノート

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