1-Ethenyl-2-(iodomethyl)benzene → 2-(Bis-methylsulfonyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-3-(2-vinyl-phenyl)-propan-1-one

HRID 2704Notes

Reaction equation

HRID 2704 reaction equation
I[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH2:10].[CH3:11][S:12]([C:15]([S:34]([CH3:37])(=[O:36])=[O:35])=[N:16][CH2:17][C:18]([N:20]1[CH:24]2[CH2:25][CH:26]3[C:29]([CH3:31])([CH3:30])[C:23]2([CH2:28][CH2:27]3)[CH2:22][S:21]1(=[O:33])=[O:32])=[O:19])(=[O:14])=[O:13]>>[CH3:11][S:12]([C:15]([S:34]([CH3:37])(=[O:36])=[O:35])=[N:16][CH:17]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH2:10])[C:18]([N:20]1[CH:24]2[CH2:25][CH:26]3[C:29]([CH3:31])([CH3:30])[C:23]2([CH2:28][CH2:27]3)[CH2:22][S:21]1(=[O:32])=[O:33])=[O:19])(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 158305741-Ethenyl-2-(iodomethyl)benzeneHCID 186125222-(Bis-methylsulfonyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-ethanone

Product 1

HCID 545027082-(Bis-methylsulfonyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-3-(2-vinyl-phenyl)-propan-1-one

Procedure

In step c, the appropriate 1-iodomethyl-2-vinyl-benzene derivative of structure (3) is subjected to an addition, elimination reaction with 2-(bis-methylsulfonyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-ethanone (4) to give the corresponding 2-(bis-methylsulfonyl-methyleneamino)-1-(10,10-dimethyl-3,3-dioxo-3-thia-4-aza-tricyclo[5.2.1.0 1,5]dec-4-yl)-3-(2-vinyl-phenyl)-propan-1-one derivative of structure (5).

Sources & evidence

ORD record
ord-5676a3bcc4df4c039dcca17382f31a6c
Source dataset
uspto-grants-1998_03
Patent number
US05731306

Reaction notes

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