Thionyl Chloride → {4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetyl chloride

HRID 81362Notes

Reaction equation

HRID 81362 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:34]=[CH:33][CH:32]=[CH:31][C:7]=1[O:8][C:9]1[N:10]=[CH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:28]=[C:27]([CH3:29])[C:21]([O:22][CH2:23][C:24](O)=[O:25])=[C:20]([CH3:30])[CH:19]=3)[O:15][C:13]=2[N:14]=1>C1(C)C=CC=CC=1>[F:5][C:6]1[CH:34]=[CH:33][CH:32]=[CH:31][C:7]=1[O:8][C:9]1[N:10]=[CH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:28]=[C:27]([CH3:29])[C:21]([O:22][CH2:23][C:24]([Cl:3])=[O:25])=[C:20]([CH3:30])[CH:19]=3)[O:15][C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53312125{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetic acid

Product 1

HCID 86679069{4-[5-(2-Fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3 ml of thionyl chloride were slowly added to 336 mg of {4-[5-(2-fluoro-phenoxy)-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenoxy}-acetic acid. The mixture was allowed to react for 2 days. Then toluene was added and the solvents were removed in vacuo. The addition and removal of toluene was repeated to give 350 mg of the title compound as a brown oil.

Workup

  1. customto react for 2 days
  2. customthe solvents were removed in vacuo
  3. additionThe addition and removal of toluene

Sources & evidence

ORD record
ord-747aa1c4782d482fbe5440a2fa05d6ff
Source dataset
uspto-grants-2014_09
Patent number
US08846690B2

Reaction notes

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