Hydrochloric Acid → 5-(2-Chloro-6-methoxyphenyl)-1,3-thiazolidine-2,4-dione

HRID 2290535ノート

反応式

HRID 2290535 の反応式
Cl[CH:2]([C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[O:14][CH3:15])[C:3]([O:5]C)=O.[NH2:16][C:17](N)=[S:18].C([OH:22])C.Cl>C(OCC)(=O)C.O>[Cl:13][C:12]1[C:7]([CH:2]2[S:18][C:17](=[O:22])[NH:16][C:3]2=[O:5])=[C:8]([O:14][CH3:15])[CH:9]=[CH:10][CH:11]=1

参加物

7

反応物 4

HCID 313Hydrochloric Acid2 回HCID 702EthanolHCID 2723790ThioureaHCID 13731103HCID 13731103、化合物

生成物 1

HCID 137311045-(2-Chloro-6-methoxyphenyl)-1,3-thiazolidine-2,4-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl alpha-chloro-alpha-(6-chloro-2-methoxyphenyl)acetate (1.37 g, 5.5 mmoles), thiourea (0.84 g, 10.0 mmoles) and ethanol (10 ml) was refluxed for 16 hours. Concentrated hydrochloric acid (4 ml) was added to the mixture and refluxing continued for an additional 16 hours. An additional 2 ml of concentrated hydrochloric acid was added and the mixture refluxed for 16 more hours. The yellow solution was then cooled to room temperature and poured into 150 ml of water. The title product was isolated by extraction of the aqueous mixture with ethyl acetate (2×150 ml). The extract was washed with water (1×50 ml) and brine (1×50 ml), then dried (MgSO4) and concentrated in vacuo to a brown oil (0.91 g). Trituration of the oil in hexane (50 ml) gave a solid which was recrystallized from ethanol-water (1:1) as a white solid, 0.0719 g. M.P. 195°-197° C.

後処理

  1. temperaturewas refluxed for 16 hours
  2. temperaturerefluxing
  3. temperaturethe mixture refluxed for 16 more hours

出典と根拠

ORDレコード
ord-7498fa59d5fe416495889d7d79f915e6
出典データセット
uspto-grants-1986_10
特許番号
US04617312

反応ノート

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