2-Amino-4-chlorobenzenethiol → HCID 136183499, compound

HRID 338793Notes

Reaction equation

HRID 338793 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([Br:20])[C:18]=1[OH:19])[CH:14]=O>CN(C=O)C>[Br:10][C:11]1[CH:12]=[C:13]([C:14]2[S:9][C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[N:1]=2)[CH:16]=[C:17]([Br:20])[C:18]=1[OH:19]

Participants

4

Reactant 2

HCID 120002-Amino-4-chlorobenzenethiolHCID 181003,5-Dibromo-4-Hydroxybenzaldehyde

Product 1

HCID 136183499HCID 136183499, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a DMF (3 mL) solvent, a solution including 2-amino-4-chlorobenzenethiol (100 mg, 0.63 mmol) and 3,5-dibromo-4-hydroxybenzaldehyde (127 mg, 0.63 mmol) was heated at a temperature of 100° C. for 8.5 hours. After DMF was evaporated therefrom, the residual was purified by silica gel column chromatography using hexane and ethyl acetate (5:1) as a developer to obtain a solid Compound 96 (34.3 mg, 18.1%).

Workup

  1. customAfter DMF was evaporated
  2. customthe residual was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-14f45b68b5ed4537a43096c870ca0811
Source dataset
uspto-grants-2014_11
Patent number
US08889881B2

Reaction notes

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