Cyanamide → benzyl 6-[(N-cyano-S-phenylsulphinimidoyl)methyl]-3-(furan-3-yl)-2-methoxybenzoate

HRID 2177864Notes

Reaction equation

HRID 2177864 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:7]([O:30][CH3:31])=[C:8]([C:19]([CH2:22][S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:21]=2)[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:2]1.[N:32]#[C:33][NH2:34].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(#N)C>[C:33]([N:34]=[S:23]([CH2:22][C:19]1[C:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])=[C:7]([O:30][CH3:31])[C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[CH:21][CH:20]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[N:32]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 12217721Iodo benzene diacetateHCID 67107722Benzyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate2×

Product 1

HCID 86677130benzyl 6-[(N-cyano-S-phenylsulphinimidoyl)methyl]-3-(furan-3-yl)-2-methoxybenzoateYield 16.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of benzyl 3-(furan-3-yl)-2-methoxy-6-(phenylthiomethyl)benzoate (Intermediate 226, 0.96 g), cyanamide (0.19 g) and iodobenzene diacetate (0.79 g) in acetonitrile (20 ml) was stirred for 16 hours. The mixture was evaporated to dryness and the residue was purified by chromatography on silica eluting with ethyl acetate and DCM with a gradient of 0-5% to give benzyl 6-[(N-cyano-S-phenylsulphinimidoyl)methyl]-3-(furan-3-yl)-2-methoxybenzoate (0.17 g) as a colourless gum.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by chromatography on silica eluting with ethyl acetate and DCM with a gradient of 0-5%

Sources & evidence

ORD record
ord-f7e97643590841f9ba3653aa8ee557c3
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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