Thionyl Chloride → 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-4'-(2-morpholinoethoxy)-2-naphthalenecarboxanilide

HRID 653807

反応式

HRID 653807 の反応式
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](O)=[O:15])[CH:5]=[CH:4][C:3]1=2.S(Cl)(Cl)=O.[NH2:22][C:23]1[CH:37]=[CH:36][C:26]([O:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1>O1CCCC1.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:36][CH:37]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2

参加物

6

反応物 3

HCID 24386Thionyl ChlorideHCID 2276385,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acidHCID 64847114-(2-Morpholinoethoxy)aniline

生成物 1

HCID 197603055,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-4'-(2-morpholinoethoxy)-2-naphthalenecarboxanilide収率 54.3%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a manner analogous to Example 1, 52.5 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalene-carboxylic acid were converted by reaction with 200 ml of thionyl chloride into the acid chloride and, after dissolution in 200 ml of tetrahydrofuran, added dropwise to a solution of 48.8 g of 4-[2-(4-amino-phenoxy)ethyl]-morpholine in 400 ml of pyridine while cooling slightly. The temperature should not rise above 30° C. After stirring at room temperature for 1 hour the reaction mixture was poured on to ice-water, extracted with ethyl acetate, the organic phase was washed with ice-cold 2N hydrochloric acid, dried and evaporated. The crystalline crude product was purified by filtration over a silica gel column (eluting agent hexane/ethyl acetate 1:4, then ethyl acetate, then ethyl acetate/ethanol =1:1) and recrystallized from hexane/ ethyl acetate. There were obtained 52 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-4'-(2-morpholinoethoxy)-2-naphthalenecarboxanilide in white crystals. m.p. 134° C.-136° C.

後処理

  1. temperaturewhile cooling slightly
  2. customrise above 30° C
  3. extractionextracted with ethyl acetate
  4. washthe organic phase was washed with ice-cold 2N hydrochloric acid
  5. customdried
  6. customevaporated
  7. filtrationThe crystalline crude product was purified by filtration over a silica gel column (
  8. washeluting agent hexane/ethyl acetate 1:4
  9. customethyl acetate, then ethyl acetate/ethanol =1:1) and recrystallized from hexane/ ethyl acetate

出典と根拠

ORDレコード
ord-09d41cb0509c4f0ea9133825edd4e2a4
出典データセット
uspto-grants-1992_07
特許番号
US05128470

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