Thionyl Chloride → HCID 21934560, compound

HRID 1241437Notes

Reaction equation

HRID 1241437 reaction equation
O[CH2:2][CH2:3][C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1.S(Cl)([Cl:16])=O>C1C=CC=CC=1>[Cl:16][CH2:2][CH2:3][C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11367331HCID 11367331, compound

Product 1

HCID 21934560HCID 21934560, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

7-(2-hydroxyethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (5.00 g) was added to thionyl chloride (25 mL) and refluxed for 12 hour in benzene (100 mL). The resulting solution was concentrated and the red oil was dissolved in CH2Cl2 and washed with NaHCO3 (satd). The CH2Cl2 layer was extracted, dried with Na2SO4, and concentrated in vacuo to afford 4.99 g (90%) of a tan solid. 1H NMR (DMSO-d6) δ 7.06 (d, 1H), 6.35 (br s, 1H), 6.33 (d, 1H), 3.86 (t, 2H), 3.25 (m, 2H), 2.87 (t, 2H), 2.62 (t, 2H), 1.75 (pentet, 2H).

Workup

  1. concentrationThe resulting solution was concentrated
  2. dissolutionthe red oil was dissolved in CH2Cl2
  3. washwashed with NaHCO3 (satd)
  4. extractionThe CH2Cl2 layer was extracted
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ad70d309fb443569251113b01b3146c
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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