1-Hydroxybenzotriazole hydrate → HCID 22612208, compound

HRID 844076Notes

Reaction equation

HRID 844076 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O.O.ON1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2N=N1.[ClH:30].C(N=[C:34]=[NH:35])C>CN(C)C=O.O>[Cl:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:34][NH:35][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[N:15][C:7]=1[O:6][C:5]1[CH:16]=[CH:17][CH:18]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

6

Reactant 3

HCID 27960291-Hydroxybenzotriazole hydrateHCID 12202642HCID 12202642, compoundHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 22612208HCID 22612208, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-methoxy-phenoxy)-nicotinic acid (0,300 grams, 1.224 mmole) 2-Chloro-benzylamine (0.166 grams, 1.160 mmole), and 1-hydroxybenzotriazole hydrate (0.173 grams, 1.283 mmole) in dry dimethylformamide (30 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.269 grams, 1.399 mmole) and stirred over night. The mixture was diluted with 200 ml water and extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to give an oil that was purified by chromatography on silica eluting with 30% ethyl acetate/hexane to give an oil which solidified on standing. (0.300 g). M.P. 71-74° C.; Anal. calcd. for C20H17N2O3Cl: C, 65.13; H, 4.65; N, 7.60. Found: C, 64.94; H, 4.69; N, 7.63.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas purified by chromatography on silica eluting with 30% ethyl acetate/hexane
  8. customto give an oil which

Sources & evidence

ORD record
ord-240666ad22db44fb824fe80ef97a85f7
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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