Dimethyl Sulfide → HCID 68843465, compound

HRID 1784872Notes

Reaction equation

HRID 1784872 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[C:13]([C:18]2[O:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[N:22]=2)[CH:12]=1)C1C=CC=CC=1.B(F)(F)F.CCOCC.CSC>C(Cl)(Cl)Cl>[O:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=[C:18]1[C:13]1[CH:12]=[C:11]([NH2:10])[CH:16]=[C:15]([Br:17])[CH:14]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 68842939HCID 68842939, compound

Product 1

HCID 68843465HCID 68843465, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (3-benzoxazol-2-yl-5-bromo-phenyl)-carbamic acid benzyl ester (0.160 g, 0.38 mmol) in chloroform (5.0 mL) at room temperature was added BF3-Et2O (0.21 g, 1.5 mmol) and dimethylsulfide (0.24 g, 3.78 mmol). The reaction mixture was stirred at room temperature for 20 hours. The solvent was removed and residue was purified by preparative TLC eluting with 3:1/hexanes:ethyl acetate to give 3-benzoxazol-2-yl-5-bromo-phenylamine (0.10 g, 92%) as a yellow solid.

Workup

  1. customThe solvent was removed
  2. customresidue was purified by preparative TLC
  3. washeluting with 3:1/hexanes

Sources & evidence

ORD record
ord-5d9107d478364f95a008861f4cb4dd11
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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