Sulfuryl chloride → 6-Amino-7-Chloro-5-Fluoro-2-Methylbenzoxazole

HRID 9870Notes

Reaction equation

HRID 9870 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[O:8][C:4]=2[CH:3]=1.S(Cl)([Cl:16])(=O)=O>C(OCC)(=O)C.C(Cl)Cl>[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[O:8][C:4]=2[C:3]=1[Cl:16]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 219887666-Amino-5-Fluoro-2-Methylbenzoxazole

Product 1

HCID 219887686-Amino-7-Chloro-5-Fluoro-2-Methylbenzoxazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

6-Amino-5-fluoro-2-methylbenzoxazole (12 g, 72.22 mMole) was dissolved in ethyl acetate (100 mL) containing dry pryidine (5.8 mL, 72.22 mMole). At room temperature and with good stirring, sulfuryl chloride (7.0 mL, 86.66 mMole) was added drop by drop over a 20-minute period. After stirring at room temperature for about 30 minutes, the reaction was diluted with ethyl acetate, washed with 2N-HCl, dried (MgSO4), filtered and concentrated to give a solid. This solid was dissolved in methylene chloride and passed through a short column of silica gel eluting with methylene chloride to give the product. Yield 5.0 g.

Workup

  1. additioncontaining
  2. customdry pryidine (5.8 mL, 72.22 mMole)
  3. washwashed with 2N-HCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid
  8. customto give the product

Sources & evidence

ORD record
ord-a08b0ceaa33a43d2bb9dfbb41ffd28e1
Source dataset
uspto-grants-2006_08
Patent number
US07091361B2

Reaction notes

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