Sodium Carbonate → 1-methyl-5-(2-thioxo-1,2-dihydrospiro[3,1-benzoxazine-4,1'-cyclobutan]-6-yl)-1H-pyrrole-2-carbonitrile

HRID 915897ノート

反応式

HRID 915897 の反応式
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]3[NH:19][C:18](=O)[O:17][C:13]4([CH2:16][CH2:15][CH2:14]4)[C:11]=3[CH:12]=2)=[CH:5][CH:4]=[C:3]1[C:21]#[N:22].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]3[NH:19][C:18](=[S:32])[O:17][C:13]4([CH2:16][CH2:15][CH2:14]4)[C:11]=3[CH:12]=2)=[CH:5][CH:4]=[C:3]1[C:21]#[N:22]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 87949Lawesson's reagentHCID 113583221-methyl-5-(2-oxo-1,2-dihydrospiro [3,1-benzoxazine-4,1'-cyclobutan]-6-yl)-1H-pyrrole-2-carbonitrile

生成物 1

HCID 104254421-methyl-5-(2-thioxo-1,2-dihydrospiro[3,1-benzoxazine-4,1'-cyclobutan]-6-yl)-1H-pyrrole-2-carbonitrile収率 99.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 1-methyl-5-(2-oxo-1,2-dihydrospiro [3,1-benzoxazine-4,1′-cyclobutan]-6-yl)-1H-pyrrole-2-carbonitrile (0.33 g, 1.1 mmol) and Lawesson's Reagent (0.23 g, 0.55 mmol) in toluene (10 mL) was heated at 100° C. Upon completion by TLC, the reaction mixture was poured into saturated sodium carbonate (100 mL) and extracted with ethyl acetate (50 mL), dried over magnesium sulfate, and concentrated. Trituration of the residue with ether (20 mL) gave 1-methyl-5-(2-thioxo-1,2-dihydrospiro[3,1-benzoxazine-4,1′-cyclobutan]-6-yl)-1H-pyrrole-2-carbonitrile (0.17 g, 49%) as a tan solid. 1H NMR (DMSO-d6): δ 12.35 (s, 1H), 7.64 (d, 1H, J=2.0 Hz), 7.51 (dd, 1H, J=8.2, 2.0 Hz), 7.15 (d, 1H, J=8.3 Hz), 7.05 (d, 1H, J=4.03 Hz), 6.43 (d, 1H, J=4.03 Hz), 3.73 (s, 3H), 2.59-2.53 (m, 2H), 2.09-2.02 (m, 2H), 1.93-1.85 (m, 2H). MS (ESI) m/z 310 ([M+H]+); MS (ESI) m/z 308 ([M−H]−); HRMS: calcd for C17H15N3OS, 309.0936; found (ESI_FT), 310.10057.

後処理

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-a897f8dd7646439fadf0188c7dce988d
出典データセット
uspto-grants-2007_09
特許番号
US07268149B2

反応ノート

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