Acetone → 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamate

HRID 1292521ノート

反応式

HRID 1292521 の反応式
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:14]3[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:20][N:21]=[C:22]=[O:23].CC(C)=O.C(Cl)Cl>CCOC(C)=O.[Cu]Cl>[CH3:20][NH:21][C:22](=[O:23])[O:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][N:11]=[C:10]([NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:14]=2[CH:15]=1

参加物

7

反応物 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 12228Methyl IsocyanateHCID 187964613-[[2-(4-Morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol

生成物 1

HCID 187964473-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamate収率 32.9%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol (1 g) and a catalytic amount of copper(I)chloride (0.05 g) in EtOAc (100 ml) was added methyl isocyanate (0.26 g). After 24 hours TLC (silica gel, 1:1:20 acetone/MeOL/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (1 l) and the filtrate was concentrated in vacuo. The residue was further purified by flash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM to yield 0.4 g of the product, m.p. 135°-136° C.

後処理

  1. filtrationThe reaction was filtered through neutral alumina eluting with EtOAc (1 l)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was further purified by flash chromatography (silica gel)
  4. washeluting with 1:1:20 acetone/MeOH/DCM

出典と根拠

ORDレコード
ord-3e4b42ccb3a94495ae4c8856feace7f3
出典データセット
uspto-grants-1998_05
特許番号
US05756754

反応ノート

読み込み中…