Triethylamine → HCID 178432498, compound

HRID 2233302Notes

Reaction equation

HRID 2233302 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[O:16][C:15]([C:17]3([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:14][C:13]=2[CH3:24])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:26][OH:27].C(N(CC)CC)C>O1CCCC1.CO>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[O:16][C:15]([C:17]3([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:14][C:13]=2[CH3:24])[CH:7]=[CH:6][C:3]=1[C:4]([NH:26][OH:27])=[NH:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59295428HCID 59295428, compound

Product 1

HCID 178432498HCID 178432498, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

1.24 g 2-Chloro-4-[4-methyl-2-(1-methyl-cyclohexyl)-oxazol-5-ylmethoxy]-benzonitrile were dissolved in a mixture of 20 ml tetrahydrofuran and 20 ml methanol. 5.0 g hydroxylamine hydrochloride were added followed by the addition of 10.0 ml triethylamine. The reaction mixture was stirred at 65° C. overnight. The solvents were removed in vacuo and the resulting residue poured into water and extracted five times with ethylacetate. The combined organic extracts were washed with brine, dried over MgSO4 and the solvent was evaporated in vacuo to obtain 1.39 g 2-Chloro-N-hydroxy-4-[4-methyl-2-(1-methyl-cyclohexyl)-oxazol-5-ylmethoxy]-benzamidine as an oil.

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe resulting residue poured into water
  3. extractionextracted five times with ethylacetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ff69c206958840c4bcfbb09ffb27d60e
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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