Methanethiol → 2-diphenylmethylamino-4,5,6,7-tetrahydro-1H-1,3-diazepine hydroiodide

HRID 46636

反応式

HRID 46636 の反応式
[IH:1].[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:9][C:10](=[NH:13])SC)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24]N.CS>ClC1C=CC=CC=1Cl.C(O)(C)C>[IH:1].[C:2]1([CH:8]([NH:9][C:10]2[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][N:13]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 878MethanethiolHCID 1045PutrescineHCID 178504030HCID 178504030、化合物

生成物 1

HCID 125034152-diphenylmethylamino-4,5,6,7-tetrahydro-1H-1,3-diazepine hydroiodide

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 72391,2-Dichlorobenzene溶媒

実験手順

A suspension of 38.43 grams (0.1 mole) of 1-diphenylmethyl-2-methylthiopseudourea hydroiodide and 8.82 grams (0.1 mole) of 1,4-diaminobutane in 500 milliliters of o-dichlorobenzene was stirred and heated under reflux overnight (about 19 hours). During the heating a reaction took place with the evolution of a basic gas and methyl mercaptan and the formation of a dark oily layer. While the mixture was still warm, the solvent was decanted from the oily layer, diluted with about 1.5 liters of ether and cooled. Scratching of the ether solution caused light colored crystals to form. The dark oily residue was taken up in about 75 milliliters of isopropanol and stored at -23° C., whereupon it came a semisolid gum; the gum was separated from the mother liquor by decantation and redissolved in fresh isopropanol whereupon a dark solid separated. The light colored crystals from the ether and the dark solid from the isopropanol were separately recrystallized using activated carbon and methanol-isopropanol mixture as solvent to obtain white crystals. The white crystals separately obtained were combined and recrystallized from the same solvent pair to obtain a purified 2-diphenylmethylamino-4,5,6,7-tetrahydro-1H-1,3-diazepine hydroiodide product m.p. 215°-217.5° C.

後処理

  1. temperatureheated
  2. temperatureunder reflux overnight (about 19 hours)
  3. temperatureWhile the mixture was still warm
  4. customthe solvent was decanted from the oily layer
  5. additiondiluted with about 1.5 liters of ether
  6. temperaturecooled
  7. customto form
  8. customstored at -23° C., whereupon it
  9. customthe gum was separated from the mother liquor by decantation
  10. dissolutionredissolved in fresh isopropanol whereupon a dark solid
  11. customseparated
  12. customThe light colored crystals from the ether and the dark solid from the isopropanol were separately recrystallized
  13. customto obtain white crystals
  14. customThe white crystals separately obtained
  15. customrecrystallized from the same solvent pair

出典と根拠

ORDレコード
ord-35e48ae9a67a438cb2acdb5ae6af086d
出典データセット
uspto-grants-1979_11
特許番号
US04174401

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