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

HRID 458557노트

반응식

HRID 458557 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-2b7aa1e571824338a5ddadb5b1cab1d0
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192956B2

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