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

HRID 1080427ノート

反応式

HRID 1080427 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.CO.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

6

反応物 3

HCID 12228Methyl IsocyanateHCID 187964613-[[2-(4-Morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-olHCID 21584259acetone MeOH DCM

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/MeOH/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-bc7f18e8b79942dba119cfb0934f429e
出典データセット
uspto-grants-1996_12
特許番号
US05580982

反応ノート

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