2-Methoxyaniline → HCID 10803061, compound

HRID 1110812Notes

Reaction equation

HRID 1110812 reaction equation
S(Cl)(Cl)=O.Cl.[CH3:6][C:7]1[NH:8][C:9]2[CH2:15][CH:14]([C:16]([OH:18])=O)[CH2:13][CH2:12][C:10]=2[N:11]=1.[CH3:19][O:20][C:21]1[C:22]([NH2:27])=[CH:23][CH:24]=[CH:25][CH:26]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:16]([CH:14]1[CH2:13][CH2:12][C:10]2[N:11]=[C:7]([CH3:6])[NH:8][C:9]=2[CH2:15]1)=[O:18]

Participants

6

Reactant 4

HCID 70002-MethoxyanilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 14856792HCID 14856792, compound

Product 1

HCID 10803061HCID 10803061, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

Thionyl chloride, 5 ml, was added to 0.50 g (0.97 mmols) of 2-methyl-4,5,6,7-tetrahydrobenzimidazole-5carboxylic acid hydrochloride (including 58 w/w % of NaCl) obtained in Reference Example 2 and the mixture was heated at 90° C. for 3 hours. After thionyl chloride was distilled off under reduced pressure, 10 ml of methylene chloride was added to the residue and at 0° to 5° C., 0.20 ml (1.78 mmol) of o-anisidine and 0.40 ml (2.89 mmols) of triethylamine were added to the mixture followed by stirring at room temperature for 16 hours. After 50 ml of methylene chloride was supplemented, the mixture was washed with 1 N sodium hydroxide solution and then dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with methylene chloride-methanol-ammonia water (10 : 1 : 0.1). The solvent was distilled off and the resulting colorless crystals were recyrstallized from ethyl acetate to give 0.10 g (37.0%) of N-(2-methyoxyphenyl)-2-methyl -4,5,6,7-tetrahydrobenzimidazole-5-carboxamide monhydrate.

Workup

  1. customobtained in Reference Example 2
  2. distillationAfter thionyl chloride was distilled off under reduced pressure, 10 ml of methylene chloride
  3. additionwas added to the residue and at 0° to 5° C.
  4. washthe mixture was washed with 1 N sodium hydroxide solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. washeluted with methylene chloride-methanol-ammonia water (10 : 1 : 0.1)
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-7c3eddef3a504461af47ee140d43c793
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

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