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

HRID 1748973Notes

Reaction equation

HRID 1748973 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[NH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[SH:22]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[S:22][C:13]3[CH:14]=[CH:15][C:16]([C:18]([F:19])([F:20])[F:21])=[CH:17][C:12]=3[N:11]=2)[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

4

Reactant 2

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

Product 1

HCID 1361834932-Bromo-4-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a N,N-dimethylformamide (DMF) solvent, a suspension of 3-bromo-4-hydroxybenzaldehyde (1.0 eq.) and 2-amino-4-(trifluoromethyl)benzenethiol (1.0 eq.) was heated at a temperature of 100° C. After cooling, DMF was removed therefrom under reduced pressure. Methylene chloride was added to the resultant solid, and the produced precipitate was filtered, and washed with methylene chloride to obtain a solid target product.

Workup

  1. temperatureAfter cooling
  2. customDMF was removed
  3. additionMethylene chloride was added to the resultant solid
  4. filtrationthe produced precipitate was filtered
  5. washwashed with methylene chloride
  6. customto obtain a solid target product

Sources & evidence

ORD record
ord-5aeb303ab1c0425abd75891a4add4b80
Source dataset
uspto-grants-2015_10
Patent number
US09155690B2

Reaction notes

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