Potassium Carbonate → 6-(4-(4-Fluorophenyl)oxazol-5-yl)benzo[d]thiazol-2-amine

HRID 1671780Notes

Reaction equation

HRID 1671780 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([N+:31]#[C-:32])S(C2C=CC(C)=CC=2)(=O)=O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CCO>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:31]=[CH:32][O:12][C:11]=2[C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH2:1])[S:3][C:4]=3[CH:10]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10827289a-Tosyl-(4-fluorobenzyl) isocyanideHCID 138215412-Aminobenzo[d]thiazole-6-carbaldehyde

Product 1

HCID 575271576-(4-(4-Fluorophenyl)oxazol-5-yl)benzo[d]thiazol-2-amineYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-aminobenzo[d]thiazole-6-carbaldehyde (0.91 g, 5.11 mmol, 1.0 eq.), 1-((4-fluorophenyl)(isocyano)methylsulfonyl)-4-methylbenzene (2.20 g, 7.60 mmol, 1.5 eq.), and K2CO3 (1.34 g, 9.70 mmol, 1.9 eq.) in EtOH (51 mL) was refluxed for 4 h. After cooling to room temperature, the reaction mixture was concentrated in vacuo, and the residue was taken up in CH2Cl2 and saturated aqueous NaHCO3. After separation of the layers, the aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (40:1) as eluent afforded 6-(4-(4-fluorophenyl)oxazol-5-yl)benzo[d]thiazol-2-amine as a tan solid (1.37 g, 86% yield).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customAfter separation of the layers
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f567ecc4a9ba41a38ff52e6d75de2a76
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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