Phenyl Isothiocyanate → N-(3-(Dimethylamino)propyl)-N'-phenylthiourea

HRID 1836743ノート

反応式

HRID 1836743 の反応式
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][N:11]([CH3:16])[CH2:12][CH2:13][CH2:14][NH2:15]>COC(C)(C)C.C(O)(C)C>[CH3:10][N:11]([CH3:16])[CH2:12][CH2:13][CH2:14][NH:15][C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[S:9]

参加物

5

反応物 2

HCID 7673Phenyl IsothiocyanateHCID 7993N,N-Dimethyl-1,3-propanediamine

生成物 1

HCID 1982459N-(3-(Dimethylamino)propyl)-N'-phenylthiourea収率 70.1%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

Phenyl isothiocyanate (5.283 g, 39.1 mmole) in 30 mL t-butyl methyl ether was added to a solution of 3-(dimethylamino)propylamine (3.993 g, 39.1 mmole) in 10 mL isopropanol. After stirring 2 hr at room temp., the solid which separated was filtered out and washed with t-butyl methyl ether to afford 6.51 g of 1-[3-(dimethylamino)propyl]-3-phenylthiourea (mp 112-114° C.), part of which (2.374 g, 10 mmole) was dissolved in ethanol (20 mL) containing conc. HCl (1.67 mL, 20 mmole) and added to 2-methylnaphthoquinone dissolved in warm ethanol (35 mL). After 4 days in a stoppered flask at room temp., the mixture was concentrated, and dissolved in ethyl acetate. The solid which separated after 16 hr was filtered out, but became sticky on the filter and was discarded. The filtrate was stored another 12 days at room temp. The powder which separated was filtered out to give 600 mg of pinkish-buff powder. Of this, 325 mg was recrystallized from 10 mL methanol+60 mL ethyl acetate containing a few drops of water to give 260 mg of the title compound, mp 238-240° C.

後処理

  1. customthe solid which separated
  2. filtrationwas filtered out
  3. washwashed with t-butyl methyl ether

出典と根拠

ORDレコード
ord-da8dcba9b8194a44ac4326c387700005
出典データセット
uspto-grants-2004_08
特許番号
US06777557B2

反応ノート

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