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Water → HCID 15171555, compound

HRID 728175
Notes
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Reaction equation

HRID 728175 reaction equation
[C:1]([NH:4][C:5]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].Cl.[NH2:13][C:14]1[O:15][C:16]2[CH:22]=[C:21]([CH2:23]Cl)[CH:20]=[CH:19][C:17]=2[N:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([NH:4][C:5]1[C:10]([O:11][CH2:23][C:21]2[CH:20]=[CH:19][C:17]3[N:18]=[C:14]([NH2:13])[O:15][C:16]=3[CH:22]=2)=[CH:9][CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 573434N-(3-hydroxypyridin-2-yl)acetamideHCID 198232972-Amino-6-chloromethylbenzoxazole hydrochloride

Product 1

HCID 15171555HCID 15171555, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-acetamido-3-hydroxypyridine (1.3 g), 2-amino-6-chloromethylbenzoxazolehydrochloride (1.5 g) and potassium carbonate (2.8 g) in N,N-dimethylformamide (20 ml) was stirred for 4.3 hours at 40° C. The reaction mixture was added to water and the mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue was crystallized from ethyl acetate to give 6-(2-acetamido-pyridin-3-yloxymethyl}-2-aminobenzoxazole (0.83 g).

Workup

  1. extractionthe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-de6fa878337d4772b0bfb805d6aa9cd3
Source dataset
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05047411

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes