Thionyl Chloride → HCID 13936003, compound

HRID 649534Notes

Reaction equation

HRID 649534 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][C:7](O)([C:11]([NH2:13])=[O:12])[C:6]=2[CH:15]=1.S(Cl)([Cl:18])=O>C(OCC)C>[Cl:18][C:7]1([C:11]([NH2:13])=[O:12])[C:6]2[CH:15]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20141812HCID 20141812, compound

Product 1

HCID 13936003HCID 13936003, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
28 °C

Procedure

A mixture consisting of 6-fluoro-4-hydroxy-3,4-dihydro-2H-1-benzopyran-4-carboxamide (60 mg, 0.28 mmol) and thionylchloride (60 mg, 0.28 mmol) in 1.0 ml of diethyl ether was stirred for 5.0 hours at 28° C. The reaction mixture was evaporated in vacuo to give a pale yellowish oil which was chromatographed on silica gel, eluting with ethyl ether to give 43 mg (67.2%) of the desired refined compound.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto give a pale yellowish oil which
  3. customwas chromatographed on silica gel
  4. washeluting with ethyl ether
  5. customto give 43 mg (67.2%) of the desired refined compound

Sources & evidence

ORD record
ord-47988a51939d4ed3a1726b53399ce6fb
Source dataset
uspto-grants-1988_04
Patent number
US04740517

Reaction notes

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