Cyclohexanecarboxamide → Cyclohexanecarbothioamide

HRID 239447

반응식

HRID 239447 반응식
[CH:1]1([C:7]([NH2:9])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:19])=CC=1>C1COCC1>[CH:1]1([C:7](=[S:19])[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 14283CyclohexanecarboxamideHCID 87949Lawesson's reagent

생성물 1

HCID 12336049Cyclohexanecarbothioamide수율 78.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Cyclohexanecarboxamide (1 g, 7.86 mmol) and Lawesson's Reagent (2 g, 4.94 mmol) in THF (50 mL) was heated at 70° C. for 3 h. Silica was added and the volatiles were removed under reduced pressure. The residue was column chromatographed with EtOAc/DCM to afford cyclohexanecarbothioamide (0.557 g, 49% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.67 (br. s., 1H), 6.91 (br. s., 1H), 2.56 (tt, J=11.8, 3.3 Hz, 1H), 1.90-2.02 (m, 2H), 1.78-1.90 (m, 2H), 1.71 (d, J=12.0 Hz, 1H), 1.51 (qd, J=12.3, 2.8 Hz, 2H), 1.16-1.40 (m, 3H), e/z (ES+): 144 [M+H]+.

후처리

  1. additionSilica was added
  2. customthe volatiles were removed under reduced pressure
  3. customchromatographed with EtOAc/DCM

출처 및 근거

ORD 기록
ord-b9b73690bbaf4a919585710921e0fb12
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642759B2

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