Thionyl Chloride → HCID 57831213, compound

HRID 1642018Notes

Reaction equation

HRID 1642018 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=1.S(Cl)([Cl:18])=O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.C(Cl)Cl>[Cl:18][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 13102467HCID 13102467, compound

Product 1

HCID 57831213HCID 57831213, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2.0 grams (0.0099 mole) of (4-pyrimidin-2-yloxyphenyl)methan-1-ol (known compound) and 7 drops of pyridine in 50 mL of methylene chloride was cooled in an ice-water bath, and 0.94 mL (0.013 mole) of thionyl chloride was added dropwise. Upon completion of the addition, the reaction mixture was stirred for 3 hours at 10° C. to 20° C. The reaction mixture was then poured into ice-water and basified using sodium bicarbonate. The aqueous layer was separated from the organic layer, and was extracted one time with 75 mL of methylene chloride. The methylene chloride extract and organic layer were combined and passed through silicone coated filter paper. The fitrate was then concentrated under reduced pressure, yielding 2.1 grams of the subject compound.

Workup

  1. additionUpon completion of the addition
  2. customThe aqueous layer was separated from the organic layer
  3. extractionwas extracted one time with 75 mL of methylene chloride
  4. extractionThe methylene chloride extract
  5. concentrationThe fitrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-baebf9c5c2bc4a35b6531ae0039f6eae
Source dataset
uspto-grants-2012_02
Patent number
US08119563B2

Reaction notes

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