N-[(4-bromophenyl)(toluene-4-sulfonyl)methyl]formamide → a-Tosyl-(4-bromobenzyl) isocyanide

HRID 32578Notes

Reaction equation

HRID 32578 reaction equation
CC1C=CC(S(C(C2C=CC=C(I)C=2)[N+]#[C-])(=O)=O)=CC=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([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:24][CH:23]=1.IC1C=C(C(NC=O)S(C2C=CC(C)=CC=2)(=O)=O)C=CC=1>>[CH3:38][C:35]1[CH:34]=[CH:33][C:32]([S:29]([CH:28]([C:25]2[CH:24]=[CH:23][C:22]([Br:21])=[CH:27][CH:26]=2)[N+:39]#[C-:40])(=[O:31])=[O:30])=[CH:37][CH:36]=1

Participants

4

Reactant 3

HCID 12181677N-[(4-bromophenyl)(toluene-4-sulfonyl)methyl]formamide2×HCID 17965763(3-Iodophenyl)(isocyano)methyl 4-methylphenyl sulfoneHCID 85929703{(3-Iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide

Product 1

HCID 2771757a-Tosyl-(4-bromobenzyl) isocyanide

Procedure

The title compound was prepared by a similar process to that described for Intermediate 53 but using {(4-bromophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide (Intermediate 65) in place of {(3-iodophenyl)[(4-methylphenyl)sulfonyl]methyl}formamide (Intermediate 52). Brown solid (3.1 g, 29%);

Sources & evidence

ORD record
ord-92deb0654af94aca83286e2e2e8a1661
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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