Anthranilic Acid → HCID 178481666, 화합물

HRID 371623노트

반응식

HRID 371623 반응식
[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

참가 물질

4

반응물 2

HCID 227Anthranilic AcidHCID 11167Methyl isothiocyanate

생성물 1

HCID 178481666HCID 178481666, 화합물수율 41.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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°.

후처리

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

출처 및 근거

ORD 기록
ord-6e540baa91684a48b353d344d0328ebd
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04087422

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