Dicyclohexylcarbodiimide → 4,4-Dimethyl-9-[4-(thiomorpholino)butyryloxy]-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[c][1]benzopyran hydrochloride

HRID 267350ノート

反応式

HRID 267350 の反応式
[CH3:1][C:2]1([CH3:25])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:24])=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1.[ClH:26].[S:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][C:36](O)=[O:37])[CH2:29][CH2:28]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:26].[CH3:25][C:2]1([CH3:1])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:24][C:36](=[O:37])[CH2:35][CH2:34][CH2:33][N:30]3[CH2:29][CH2:28][S:27][CH2:32][CH2:31]3)=[CH:12][C:13]([CH:15]([CH:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:14][C:4]=2[O:3]1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 215348Cyclopenta(c)(1)benzopyran-9-ol, 1,2,3,4-tetrahydro-4,4-dimethyl-7-(1,2-dimethylheptyl)-HCID 70633382gamma-Thiomorpholinobutyric acid hydrochloride

生成物 1

HCID 681357664,4-Dimethyl-9-[4-(thiomorpholino)butyryloxy]-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[c][1]benzopyran hydrochloride収率 35%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1.5 g. (4.4 mmole) of 4,4-dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[ c][1]benzopyran, 0.99 g. (4.4 mmole) of γ-thiomorpholinobutyric acid hydrochloride, and 0.99 g. (4.8 mmole) of dicyclohexylcarbodiimide in 125 ml. of methylene chloride was stirred and heated at reflux for 16 hours. The reaction mixture was cooled and the byproduct of dicyclohexylurea was removed by suction filtration. The solvents were evaporated to give a residue which crystallized from a mixture of 10 ml. chloroform/40 ml. diethyl ether to give 0.85 g. (35%) of the desired product as a beige solid, m.p. 167°-171°C. The material was pure by thin layer chromatography, and the infrared and nuclear magnetic resonance spectra were in agreement with the proposed structure.

後処理

  1. additionA mixture of 1.5 g
  2. temperatureheated
  3. temperatureat reflux for 16 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe byproduct of dicyclohexylurea was removed by suction filtration
  6. customThe solvents were evaporated
  7. customto give a residue which
  8. customcrystallized from a mixture of 10 ml
  9. customdiethyl ether to give 0.85 g

出典と根拠

ORDレコード
ord-848c5b9b4e2c419684df6ef0e345a49a
出典データセット
uspto-grants-1976_03
特許番号
US03941782

反応ノート

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