Methanol → HCID 18771474, compound

HRID 1387639Notes

Reaction equation

HRID 1387639 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.O=S(Cl)Cl.[CH3:16][S:17](Cl)(=[O:19])=[O:18].[CH3:21]O>>[CH3:16][S:17]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:21])=[O:8])=[CH:10][CH:11]=1)(=[O:19])=[O:18]

Participants

5

Reactant 4

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 31297Methanesulfonyl chlorideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 18771474HCID 18771474, compound

Procedure

To a suspension of 4-(aminomethyl)benzoic acid (10 g, 66 mmol) in MeOH (100 mL) at 0° C. was added SOCl2 (5.3 mL, 73 mmol) dropwise. The ice bath was removed and the reaction stirred at rt overnight. After heating the reaction at reflux for 4 h, the solvent was evaporated. The residue was suspended in CH2Cl2 (100 mL) at 0° C. and triethylamine (25 mL) was added, followed by the dropwise addition of methanesulfonyl chloride (7.75 mL, 100 mmol). The reaction was stirred at rt for 1 h, poured into ice H2O, extracted with CH2Cl2, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel eluting with 1% MeOH/CHCl3. The title compound was isolated as a white solid (11.8 g, 74%): 1H NMR (CDCl3): d 8.03 (d, 2H); 7.42 (d, 2H); 4.9 (br t, 1H); 4.38 (d, 2H); 3.92 (s, 3H); 2.89 (s, 3H).

Workup

  1. customThe ice bath was removed
  2. temperatureAfter heating
  3. customthe reaction
  4. temperatureat reflux for 4 h
  5. customthe solvent was evaporated
  6. customwas suspended in CH2Cl2 (100 mL) at 0° C.
  7. additiontriethylamine (25 mL) was added
  8. stirringThe reaction was stirred at rt for 1 h
  9. extractionextracted with CH2Cl2
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. customevaporated
  13. customchromatographed on silica gel eluting with 1% MeOH/CHCl3

Sources & evidence

ORD record
ord-59ec22e5769c4a1086352eb813f7bfe3
Source dataset
uspto-grants-2001_07
Patent number
US06268370B1

Reaction notes

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