Iodine chloride → 2-Methoxy-5-Methylaniline

HRID 730550Notes

Reaction equation

HRID 730550 reaction equation
ICl.C1C(=O)N(Br)C(=O)C1.IC1C2OC=CC=2C=C(S([NH:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=2[O:32][CH3:33])(=O)=O)C=1>>[CH3:31][C:29]1[CH:28]=[CH:27][C:26]([O:32][CH3:33])=[C:25]([NH2:24])[CH:30]=1

Participants

4

Reactant 3

HCID 24640Iodine chlorideHCID 67184N-bromobutanimideHCID 668925067-Iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide

Product 1

HCID 84452-Methoxy-5-Methylaniline

Procedure

7-iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide is produced starting from 2,3-dihydrobensofuran. Treatment with chlorosulfonic acid gives the corresponding sulfonyl chloride, which is iodinated using iodine monochloride. Aromatization is done using NBS, resulting in 7-iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide after treatment with cresidine.

Sources & evidence

ORD record
ord-976addb137994549b4eb022567162e52
Source dataset
uspto-grants-2009_09
Patent number
US07582767B2

Reaction notes

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