N-((3-bromophenyl)(tosyl)methyl)formamide → 1-Bromo-3-(isocyano(tosyl)methyl)benzene

HRID 32569Notes

Reaction equation

HRID 32569 reaction equation
CC1C=CC(S(C(C2C=CC=C(I)C=2)[N+]#[C-])(=O)=O)=CC=1.[Br:21][C:22]1[CH:23]=[C:24]([CH:28]([NH:39][CH:40]=O)[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:25]=[CH:26][CH:27]=1.IC1C=C(C(NC=O)S(C2C=CC(C)=CC=2)(=O)=O)C=CC=1>>[CH3:38][C:35]1[CH:36]=[CH:37][C:32]([S:29]([CH:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([Br:21])[CH:23]=2)[N+:39]#[C-:40])(=[O:31])=[O:30])=[CH:33][CH:34]=1

Participants

4

Reactant 3

HCID 11337611N-((3-bromophenyl)(tosyl)methyl)formamide2×HCID 17965763(3-Iodophenyl)(isocyano)methyl 4-methylphenyl sulfoneHCID 85929703{(3-Iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide

Product 1

HCID 27717851-Bromo-3-(isocyano(tosyl)methyl)benzene

Procedure

The title compound was prepared by a similar process to that described for Intermediate 53 but using {(3-bromophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide (Intermediate 56) in place of {(3-iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide (Intermediate 52). Light brown solid (3.2 g, 30%);

Sources & evidence

ORD record
ord-14662cabbe2e4582ba1fa9fd3dbb6c38
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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