Chloride → 1-(1-Naphthoyl)-3-[4-(5,6,7,8-tetrahydro-2-naphthyl)-2-thiazolyl]thiourea

HRID 1463844ノート

反応式

HRID 1463844 の反応式
[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[S-:15][C:16]#[N:17].[NH4+].[NH2:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:34]=[CH:33][C:32]3[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=3[CH:26]=2)[N:24]=1>CN(C=O)C.C1COCC1.CC(C)=O.O>[C:1]1([C:11]([NH:17][C:16]([NH:19][C:20]2[S:21][CH:22]=[C:23]([C:25]3[CH:34]=[CH:33][C:32]4[CH2:31][CH2:30][CH2:29][CH2:28][C:27]=4[CH:26]=3)[N:24]=2)=[S:15])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

9

反応物 4

HCID 312ChlorideHCID 68471-Naphthoic acidHCID 15666Ammonium thiocyanateHCID 7350912-Amino-4-(5,6,7,8-tetrahydro-2-naphthyl)thiazole

生成物 1

HCID 190887481-(1-Naphthoyl)-3-[4-(5,6,7,8-tetrahydro-2-naphthyl)-2-thiazolyl]thiourea収率 45.4%

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 180Acetone溶媒3 回HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

DMF (1 drop) was added to a solution of 1-naphthoic acid (900 mg) in THF (10 ml), followed by addition of oxayly chloride (0.49 ml) and stirring at room temperature for 2 hours. After replacing the solvent with acetone (10 ml), a solution of ammonium thiocyanate (436 mg) in acetone (5 ml) was added to the solution, followed by heating over a warm water bath for 1 minute and stirring at room temperature for 20 minutes. Then, a solution of 2-amino-4-(5,6,7,8-tetrahydro-2-naphthyl)thiazole (1,00 g) in acetone (10 ml) was added to the mixed solution, which was then stirred at room temperature for 16 hours. The reaction solution was poured into water, and the crystals which separated out were recovered by filtration and washed with diethyl ether. Recrystallization from dichloroethane-ethanol produced 1-(1-naphthoyl)-3-[4-(5,6,7,8-tetrahydro-2-naphthyl)-2-thiazolyl]thiourea (yield of 875 mg, 45.4%) in the form of colorless needles. m.p. 216°-217° C.

後処理

  1. temperatureby heating over a warm water bath for 1 minute
  2. stirringstirring at room temperature for 20 minutes
  3. stirringwas then stirred at room temperature for 16 hours
  4. customthe crystals which separated out
  5. filtrationwere recovered by filtration
  6. washwashed with diethyl ether
  7. customRecrystallization from dichloroethane-ethanol

出典と根拠

ORDレコード
ord-191cd670c6804b1ead7a1d542bb0b7f9
出典データセット
uspto-grants-1994_04
特許番号
US05302608

反応ノート

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