2-Methoxyaniline → HCID 21641423, compound

HRID 1110811Notes

Reaction equation

HRID 1110811 reaction equation
S(Cl)(Cl)=[O:2].Cl.C[N:7]1[C:11]2[CH2:12][CH2:13][CH:14]([C:16]([OH:18])=O)[CH2:15][C:10]=2[N:9]=[CH:8]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>ClCCl>[OH2:2].[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:11]2[N:7]=[CH:8][NH:9][C:10]=2[CH2:15]1)=[O:18]

Participants

6

Reactant 4

HCID 70002-MethoxyanilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 14856791HCID 14856791, compound

Product 1

HCID 21641423HCID 21641423, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

Thionyl chloride, 10 ml, was added to 1.4 g (2.7 mmols) of 1-methyl-4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid hydrochloride (including NaCl) obtained in Reference Example 1 and the mixture was heated at 90° C. for 4 hours. After thionyl chloride was distilled off under reduced pressure, 10 ml of dichloromethane was added to the residue and at 0° to 4° C., 0.50 ml (4.4 mmols) of o-anisidine and 1.0 ml (7.2 mmols) of triethylamine were added to the mixture followed by stirring at room temperature for 21 hours. After 40 ml of dichloromethane was added to the reaction mixture, 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 dichloromethane methanol-ammonia water (10 : 1 : 0.1). The solvent was distilled off and the resulting crystals were recyrstallized from ethyl acetate to give 0.18 g of N-(2-methyoxyphenyl)-4,5,6,7-tetrahydrobenzimidazole -5-carboxamide hydrate.

Workup

  1. customobtained in Reference Example 1
  2. distillationAfter thionyl chloride was distilled off under reduced pressure, 10 ml of dichloromethane
  3. additionwas added to the residue and at 0° to 4° 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 dichloromethane methanol-ammonia water (10 : 1 : 0.1)
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-8c615148590643548c911c7a852923d1
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

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