2-Thiopheneglyoxylic acid → 2-Hydroxyimino(thien-2-yl)acetic acid

HRID 1729969

反応式

HRID 1729969 の反応式
[OH:1][NH:2]Cl.C(=O)(O)[O-].[Na+].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=O)[C:15]([OH:17])=[O:16]>O>[OH:1][N:2]=[C:14]([C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)[C:15]([OH:17])=[O:16]

参加物

5

反応物 3

HCID 776942-Thiopheneglyoxylic acidHCID 149953Hydroxylamine, N-chloro-HCID 516892Sodium Bicarbonate2 回

生成物 1

HCID 736296442-Hydroxyimino(thien-2-yl)acetic acid収率 51%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A cooled solution of hydroxylamino hydrochloride (0.884 g) and sodium bicarbonate (1.08 g) in water (20 ml.) was added to a cooled (0°) solution of thien-2-yl-glyoxylic acid (2.0 g) and sodium bicarbonate (1.08 g) in water (20 ml.). After two days at 20° the solution was extracted with ether, cooled and acidified with concentrated hydrochloric acid. The resulting white solid was filtered off (0.564 g) and the filtrate was then thoroughly extracted with ether. The combined extracts were washed with brine, dried and concentrated. The solid residue was triturated with benzene to give the oxime (syn-isomer) (1.05 g; 51%), m.p. 1320,λmax. (ethanol) 284 mm (ε9,500), νmax. (Nujol) 2590 and 1706 (CO2H) and 1655 cm-1 (C=N), (DMSO-d6), -2.5 to -9.5 (broad multiplet; N-OH and COOH), 2.36 (multiplet; thienyl C-5 H) and 2.82 (multiplet; thienyl C-3 H and C-4 H).

後処理

  1. extractionAfter two days at 20° the solution was extracted with ether
  2. temperaturecooled
  3. filtrationThe resulting white solid was filtered off (0.564 g)
  4. extractionthe filtrate was then thoroughly extracted with ether
  5. washThe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe solid residue was triturated with benzene

出典と根拠

ORDレコード
ord-21d1ee193ee941c89a2135d4a666f620
出典データセット
uspto-grants-1976_11
特許番号
US03991046

関連ノート

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