Triethylamine → HCID 178432455, compound

HRID 2233313Notes

Reaction equation

HRID 2233313 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([Cl:18])[CH:11]=2)=[C:5]([CH3:7])[N:6]=1.Cl.[NH2:20][OH:21].C(N(CC)CC)C>O1CCCC1.CO>[Br:1][C:2]1[S:3][C:4]([CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]([NH:20][OH:21])=[NH:15])=[C:12]([Cl:18])[CH:11]=2)=[C:5]([CH3:7])[N:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59295488HCID 59295488, compound

Product 1

HCID 178432455HCID 178432455, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

4-(2-Bromo-4-methyl-thiazol-5-ylmethoxy)-2-chloro-benzonitrile (200 mg, 0.6 mmol) was dissolved in a mixture of 4 ml tetrahydrofuran and 4 ml methanol. Hydroxylamine hydrochloride (1.0 g, 14.6 mmol) was added followed by the addition of 2.1 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 199 mg 4-(2-Bromo-4-methyl-thiazol-5-ylmethoxy)-2-chloro-N-hydroxy-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-260b1e6f82d449c7b139ce69c354c360
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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