3-Bromo-4-hydroxybenzaldehyde → 2-Bromo-4-(5-(trifluoromethyl)-2,3-dihydrobenzo[d]thiazol-2-yl)phenol

HRID 1748997

Reaction equation

HRID 1748997 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[SH:12].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[OH:22])[CH:17]=O>CN(C=O)C>[Br:13][C:14]1[CH:15]=[C:16]([CH:17]2[NH:1][C:2]3[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=3[S:12]2)[CH:19]=[CH:20][C:21]=1[OH:22]

Participants

4

Reactant 2

HCID 763083-Bromo-4-hydroxybenzaldehydeHCID 880422-Amino-4-(trifluoromethyl)benzenethiol

Product 1

HCID 601946862-Bromo-4-(5-(trifluoromethyl)-2,3-dihydrobenzo[d]thiazol-2-yl)phenolYield 10.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a DMF (3 mL) solvent, a solution including 2-amino-4-trifluoromethylbenzenethiol (100 mg, 0.44 mmol) and 3-bromo-4-hydroxybenzaldehyde (88.4 mg, 0.44 mmol) was heated at a temperature of 100° C. for 2.5 hours. After DMF was evaporated, the residual was distributed between methylene chloride and water, and an organic layer was evaporated. The produced solid was filtered, and washed with ethyl acetate to obtain a solid Compound 119.

Workup

  1. customAfter DMF was evaporated
  2. customan organic layer was evaporated
  3. filtrationThe produced solid was filtered
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-46b0224d80724a758a90847126765465
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Linked notes

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