Toluene → HCID 178484345, compound

HRID 2402006Notes

Reaction equation

HRID 2402006 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:15]([NH2:17])=[O:16])=[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:6]=1.C1(C)C=CC=CC=1.CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>>[Br:1][C:2]1[S:3][C:4]([C:15](/[N:17]=[CH:27]\[N:28]([CH3:30])[CH3:29])=[O:16])=[C:5]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=2)[N:6]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 66748009HCID 66748009, compound

Product 1

HCID 178484345HCID 178484345, compound

Conditions

Temperature
50 °C

Procedure

In a 250 mL round bottomed flask were placed 2-bromo-4-(4-chlorobenzyl)-1,3-thiazole-5-carboxamide (0.66 g, 2.0 mmol) and toluene (30 mL, 300 mmol). The mixture was turned into a suspension by ultrasonication. To the suspension was added 1,1-dimethoxy-N,N-dimethylmethanamine (80 uL, 6.0 mmol) and the mixture was stirred for 2 h at 50° C. The mixture was allowed to cool to rt then was concentrated under reduced pressure. The residue was used in the next step without further purification. LC/MS (FA) ES+ 388.

Workup

  1. customIn a 250 mL round bottomed flask were placed
  2. customThe mixture was turned into a suspension by ultrasonication
  3. temperatureto cool to rt
  4. concentrationthen was concentrated under reduced pressure
  5. customThe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-59d60dce8c5d4fdca96bdb5e97cec174
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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