2-Aminothiazole → HCID 59732908, compound

HRID 560024Notes

Reaction equation

HRID 560024 reaction equation
FC1C=CC=C(OC)C=1OC1C=CC(C)=CC=1[N+]([O-])=O.BrN1C(=O)CCC1=O.C(OO[C:39](=[O:46])C1C=CC=CC=1)(=O)C1C=CC=CC=1.CS([O-])=O.[Na+].[F:52][C:53]1[CH:71]=[CH:70][CH:69]=[C:68]([O:72][CH3:73])[C:54]=1[O:55][C:56]1[CH:62]=[CH:61][C:60]([CH2:63][S:64]([CH3:67])(=[O:66])=[O:65])=[CH:59][C:57]=1[NH2:58].[NH2:74][C:75]1[S:76][CH:77]=[CH:78][N:79]=1>C(Cl)(Cl)(Cl)Cl.C1COCC1>[F:52][C:53]1[CH:71]=[CH:70][CH:69]=[C:68]([O:72][CH3:73])[C:54]=1[O:55][C:56]1[CH:62]=[CH:61][C:60]([CH2:63][S:64]([CH3:67])(=[O:66])=[O:65])=[CH:59][C:57]=1[NH:58][C:39]([NH:74][C:75]1[S:76][CH:77]=[CH:78][N:79]=1)=[O:46]

Participants

9

Reactant 6

HCID 21552-AminothiazoleHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2733271Sodium methanesulfinateHCID 66998702HCID 66998702, compoundHCID 66999182HCID 66999182, compound

Product 1

HCID 59732908HCID 59732908, compoundYield 740.4%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-Fluoro-6-methoxyphenoxy)-3-nitrotoluene (0.28 g, 1.0 mmol) was heated with N-bromosuccinimide (200 mg, 1.1 mmol) and dibenzoyl peroxide (10 mg) in CCl4 (10 mL) at 90° C. for 3 hr. The reaction mixture was cooled, filtered and the filtrate was concentrated. To this residue was added sodium methanesulfinate (110 mg, 1.1 mmol) in THF (5 mL) and the mixture was heated at 60° C. for 4 hr. The volatiles were removed under reduced pressure. The residue was dissolved in ethyl acetate and was washed (brine), dried (Na2SO4) and concentrated. The resulting nitrobenzene was reduced to 2-(2-fluoro-6-methoxy-phenoxy)-5-methanesulfonylmethyl-aniline (210 mg, 65%) following the general procedure B. 1-[2-(2-Fluoro-6-methoxy-phenoxy)-5-methanesulfonylmethyl-phenyl]-3-thiazol-2-yl-urea (138 mg, 61%) was prepared from 2-(2-fluoro-6-methoxy-phenoxy)-5-methanesulfonylmethyl-aniline (162 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customThe volatiles were removed under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwas washed (brine)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e0e35608c2d24dcf8341ddd72c8182aa
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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