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

HRID 1452947Notes

Reaction equation

HRID 1452947 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-8a95beb7ee074a338781c9df86fff944
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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