2-Amino-5-methylphenol → 2-bromo-4,5,6,7-tetrahydro-N-(2-hydroxy-4-methylphenyl)-benzo[b]thiophene-3-carboxamide

HRID 1281832Notes

Reaction equation

HRID 1281832 reaction equation
[Br:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([OH:13])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[OH:22]>S(Cl)(Cl)=O>[Br:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[OH:22])=[O:13]

Participants

4

Reactant 2

HCID 760822-Amino-5-methylphenolHCID 184221372-Bromo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid

Product 1

HCID 184222082-bromo-4,5,6,7-tetrahydro-N-(2-hydroxy-4-methylphenyl)-benzo[b]thiophene-3-carboxamideYield 68.9%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

In the same manner as in Starting Material Synthesis Example 60 and using 2-bromo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (6 g), thionyl chloride (30 ml), 2-amino-5-methylphenol (3.14 g), 2-bromo-4,5,6,7-tetrahydro-N-(2-hydroxy-4-methylphenyl)-benzo[b]thiophene-3-carboxamide (5.8 g) was obtained.

Workup

  1. customMaterial Synthesis Example 60

Sources & evidence

ORD record
ord-367cd89ed591487685587ca52050b533
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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