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

HRID 338809
Notes
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Reaction equation

HRID 338809 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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)phenol

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 obain 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-072af3e54f1840808a101805588a7fcc
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889881B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes