Anthranilic Acid → HCID 178481666、化合物

HRID 371623ノート

反応式

HRID 371623 の反応式
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][N:12]=[C:13]=[S:14]>C(O)C>[SH:14][C:13]1[N:12]([CH3:11])[C:1](=[O:10])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=1

参加物

4

反応物 2

HCID 227Anthranilic AcidHCID 11167Methyl isothiocyanate

生成物 1

HCID 178481666HCID 178481666、化合物収率 41.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of anthranilic acid (22.5 g), methyl isothiocyanate (12.5 g) and ethanol (200 ml) was refluxed for 3 hours, cooled and the precipitate filtered off and washed with water. Recrystallisation from ethanol gave 2-mercapto-3-methyl-3,4-dihydroquinazolin-4-one (13.0 g, m.p. 265°-266°). A mixture of this material (5.76 g) hydrazine hydrate (20 ml) and ethanol (30 ml) was refluxed for 30 minutes, then cooled. The precipitate was filtered off, washed with water and dried to give the 2-hydrazinoquinazolinone (3.16 g, m.p. 220°-223°). Recrystallisation from ethanol gave material m.p. 223°. A stirred solution of the crude product (1.9 g) in a mixture of hydrochloric acid (20 ml, 2N) and acetic acid (10 ml) was treated dropwise at 0°-5° with a solution of sodium nitrite (0.69 g) in water (5 ml). The mixture was allowed to attain room temperature and, after 1 hour, was filtered and the precipitate washed with water and dried to give the title compound (1.04 g., m.p. 164°-167°). Recrystallisation from ethanol gave material m.p. 167°.

後処理

  1. temperaturewas refluxed for 3 hours
  2. temperaturecooled
  3. filtrationthe precipitate filtered off
  4. washwashed with water
  5. customRecrystallisation from ethanol

出典と根拠

ORDレコード
ord-6e540baa91684a48b353d344d0328ebd
出典データセット
uspto-grants-1978_05
特許番号
US04087422

反応ノート

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