Thionyl Chloride → HCID 21886113, compound

HRID 2216213Notes

Reaction equation

HRID 2216213 reaction equation
S(Cl)(Cl)=O.[I:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=O.C(N(C(C)C)CC)(C)C.[N:25]1([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[NH4+].[Cl-]>C1COCC1.C(Cl)Cl.CCOC(C)=O>[I:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([NH:34][CH2:33][CH2:32][CH2:31][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:11]

Participants

9

Reactant 5

HCID 24386Thionyl ChlorideHCID 25517Ammonium ChlorideHCID 61055N-(3-Aminopropyl)morpholineHCID 81531DiisopropylethylamineHCID 6216403-Iodo-4-methylbenzoic acid

Product 1

HCID 21886113HCID 21886113, compoundYield 50.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Thionyl chloride (5.6 mL) was added over 1 min to a 0° C. solution of 3-iodo-4-methyl benzoic acid (5 g, 19.1 mmol) in THF (30 mL). The solution was stirred for 24 h at rt and the volatile components were removed in vacuo. A portion of the crude acid chloride (1 g, 3.57 mmol) was dissolved in DCM (10 mL) and was cooled to 0° C. Diisopropylethylamine (0.78 mL, 4.46 mmol) was added followed by 3-morpholin-4-yl-propylamine (0.52 mL, 3.56 mmol) and the reaction was stirred for 1 h at rt. EtOAc (80 mL) and aq. NH4Cl (20 mL) was added and the layers were separated. The organic layer was washed with aq NH4Cl (2×10 mL), NaOH (1N, 3×20 mL), water (20 mL), brine (50 mL) and was dried over sodium sulfate. Concentration of the solution and SiO2 flash column chromatography of the residue (0–10% MeOH in DCM) yielded the product (695 mg, 50%) as a yellow glass.

Workup

  1. customthe volatile components were removed in vacuo
  2. temperaturewas cooled to 0° C
  3. stirringthe reaction was stirred for 1 h at rt
  4. customthe layers were separated
  5. washThe organic layer was washed with aq NH4Cl (2×10 mL), NaOH (1N, 3×20 mL), water (20 mL), brine (50 mL)
  6. dry with materialwas dried over sodium sulfate

Sources & evidence

ORD record
ord-b22fea5fd14542c1898161a6d190cb5d
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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