Hydroxyamine hydrochloride → HCID 178472866, compound

HRID 1274222Notes

Reaction equation

HRID 1274222 reaction equation
Cl.[NH2:2][OH:3].[NH:4]1[C:8]([CH2:9][C:10]2[S:14][C:13]([C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)=[N:7][N:6]=[N:5]1>C(O)C>[NH:4]1[C:8]([CH2:9][C:10]2[S:14][C:13]([C:15](=[N:2][OH:3])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)=[N:7][N:6]=[N:5]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178472965HCID 178472965, compound

Product 1

HCID 178472866HCID 178472866, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (205 mg) was added to a stirred mixture of ethyl 2-[5-(1-tetrazolylmethyl)thien-2-yl]-2-oxoacetate (Description 50) (394 mg) and ethanol (10 ml). The mixture was left at room temperature for 3 days, then the solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water and brine and dried over magnesium sulphate. The solution was evaporated to give the product (376 mg) as a mixture of isomers. νmax (nujol) 3131, 1746, 1724 cm-1. δ (CD3COCD3), 1.31-1.39 (3H, m), 4.36 and 4.42 (2H, two q's, J 7.22 Hz), 6.02 and 6.08 (2H, two s's), 7.10 and 7.25 (1H, two d's, J 3.73 Hz), 7.31 and 7.78 (1H, two d's, J 3.98 Hz), 9.26 and 9.30 (1H, two s's), 11.14 and 12.25 (1H, two broad s's). m/z 280 (M-H)-. [Found: m/z 281.0584. Calc. for C10H11N5O3S; 281.0583].

Workup

  1. customthe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solution was evaporated

Sources & evidence

ORD record
ord-ad313b8f31914280bad7d5568dd31bf1
Source dataset
uspto-grants-2000_12
Patent number
US06156774

Reaction notes

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