Methylamine → HCID 19876074, compound

HRID 1886379Notes

Reaction equation

HRID 1886379 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[CH:5]=[C:6]([C:10]2([C:17]([S:19]C)=S)[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:7]=[N:8][CH:9]=1>C(O)C.ClCCl>[CH3:1][NH:2][C:17]([C:10]1([C:6]2[CH:7]=[N:8][CH:9]=[C:4]([Br:3])[CH:5]=2)[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:16])=[S:19]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 54189649HCID 54189649, compound

Product 1

HCID 19876074HCID 19876074, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A 33% w/v solution of methylamine in ethanol (5.7 ml) was added dropwise to a stirred solution of 2-(5-bromopyrid-3-yl)-2-methylthiothiocarbonylcyclohexanone (1.33 g, 3.86 mmol) in ethanol (25 ml) and dichloromethane (25 ml) at 0°-5° C. The solution was stirred at room temperature for 5 hours and concentrated in vacuo at 30°-35° C. The residue was purified by flash chromatography over silica gel eluting with ethyl acetate: hexane 4:6 to give (±)-N-methyl-2-oxo-1-(5-bromopyrid-3-yl) -cyclohexanecarbothioamide (0.57 g) m.p. 201°-3° C. NMR(CDCl3) 1.68-2.16(m,4H); 2.46-2.6(m,2H); 2.66-2.8(m,2H); 3.17-3.17-3.19 (d,3H); 7.74-7.78(dd,1H); 8.38-8.39(d,1H), 8.58-8.59(d,1H); 8.8-9.0(broad singlet). Calculated for 47.7%; H,4.6%; N,8.6%. Found C, 48.2%; H,4.7%; N,8.5%.

Workup

  1. concentrationconcentrated in vacuo at 30°-35° C
  2. customThe residue was purified by flash chromatography over silica gel eluting with ethyl acetate: hexane 4:6

Sources & evidence

ORD record
ord-8b0f96f6bb294418a06d5d84e6f14d9c
Source dataset
uspto-grants-1992_09
Patent number
US05151436

Reaction notes

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