Hydrochloric Acid → HCID 11370527, compound

HRID 491703Notes

Reaction equation

HRID 491703 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH2:22].C(N(CC)CC)C.Cl>O.C1COCC1>[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH:22][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:3]=1[O:2][CH3:1]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 76132,5-DimethoxyanilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 760272,5-Dimethoxybenzoic acid

Product 1

HCID 11370527HCID 11370527, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,5-dimethoxybenzoic acid (5.0 g, 27.5 mmol) and thionyl chloride (15 mL) was refluxed for 1 h. The volatiles were removed under vacuum. The residue was dissolved in THF (20 mL and added into a cold (0° C.) solution of 2,5-dimethoxyaniline (4-6 g, 30.2 mmol), triethylamine (5 mL, 35.9 mmol) and THF (40 mL). The mixture was stirred for 30 min, poured into water, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 2/1) gave a white solid (8.1 g, 93% yield, m.p. 121-123° C.); MS m/e 318 (M+H)+.

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe volatiles were removed under vacuum
  3. dissolutionThe residue was dissolved in THF (20 mL
  4. extractionextracted with EtOAc
  5. dry with materialThe organic extracts were dried over MgSO4
  6. customEvaporation and purification by flash chromatography (hexanes/EtOAc 2/1)

Sources & evidence

ORD record
ord-000795998bdb4d349fabd0578831387a
Source dataset
uspto-grants-2009_05
Patent number
US07531564B2

Reaction notes

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