Thionyl Chloride → 3-Methylthio-8-oxo-6-(2-allyloxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

HRID 728026ノート

反応式

HRID 728026 の反応式
[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]([C:10]([O:12]CC)=O)=[C:7](Cl)[N:8]=1.CSC1NC(=O)C(C(OCC)=O)=NN=1.S(Cl)(Cl)=O.Cl.[CH2:34]([O:37][C:38]1[CH:46]=[CH:45][CH:44]=[CH:43][C:39]=1[C:40]([NH2:42])=[NH:41])[CH:35]=[CH2:36]>C(#N)C.C(N(CC)CC)C>[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]2[C:10](=[O:12])[NH:42][C:40]([C:39]3[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=3[O:37][CH2:34][CH:35]=[CH2:36])=[N:41][C:7]=2[N:8]=1

参加物

7

反応物 4

HCID 24386Thionyl Chloride2 回HCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-CarboxylateHCID 224623842-Allyloxybenzamidine hydrochlorideHCID 135478883Ethyl 5-hydroxy-3-(methylthio)-1,2,4-triazine-6-carboxylate

生成物 1

HCID 1356708043-Methylthio-8-oxo-6-(2-allyloxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒2 回

実験手順

A cooled (5° C.) solution of 3-methylthio-5-chloro-6-carboethoxy-1,2,4-triazine (prepared by heating 3-methylthio-5-oxo-6-carboethoxy-4,5-dihydro-1,2,4-triazine, 1.5 g, with thionyl chloride, 30 ml, under reflux for two hours and thereafter removing thionyl chloride) in acetonitrile (30 ml) was added to a cooled stirred mixture of 2-allyloxybenzamidine hydrochloride (2.23 g) and triethylamine (1.06 g) in acetonitrile (50 ml). The mixture was stirred with cooling (0°-5° C.) for 15 minutes, then more triethylamine (0.71 g) was added and the reaction mixture was stirred at ambient temperature for two hours and left standing overnight. A yellow precipitate was collected, washed with water and recrystallised from acetonitrile and then from acetonitrile/ethanol (50%) to afford the title compound, 0.35 g, m.p. 238°-239° C.

後処理

  1. customprepared
  2. stirringThe mixture was stirred
  3. temperaturewith cooling (0°-5° C.) for 15 minutes
  4. stirringthe reaction mixture was stirred at ambient temperature for two hours
  5. waitleft
  6. customA yellow precipitate was collected
  7. washwashed with water
  8. customrecrystallised from acetonitrile

出典と根拠

ORDレコード
ord-8e5aff8017bd4f6d8bbda98f2dc95b03
出典データセット
uspto-grants-1991_09
特許番号
US05047404

反応ノート

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