2-Amino-5-bromobenzoic acid → HCID 4444271、化合物

HRID 1108250ノート

反応式

HRID 1108250 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(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

4

反応物 2

HCID 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 triethylarine (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. IH 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-551cd97bcd5146e39f57fa1a6fb09f6e
出典データセット
uspto-grants-2000_05
特許番号
US06066638

反応ノート

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