Hydroxyamine hydrochloride → HCID 136388383, compound

HRID 1005710Notes

Reaction equation

HRID 1005710 reaction equation
[C:1]1([C:7]([C:9]2[C:10]3[S:21][CH:20]=[CH:19][C:11]=3[N:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:23][OH:24]>N1C=CC=CC=1>[C:1]1([C:7]([C:9]2[C:10]3[S:21][CH:20]=[CH:19][C:11]=3[N:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)=[N:23][OH:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22674379HCID 22674379, compound

Product 1

HCID 136388383HCID 136388383, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of phenyl 2-trifluoromethylthieno[3,2-d]pyrimidin-4-ylmethanone (60 mg, 0.19 mmol) and hydroxylamine hydrochloride (0.04 g, 0.58 mmol) in pyridine (2 mL) was refluxed for 1 h, concentrated in vacuo, treated with toluene (2 mL), concentrated in vacuo and the resulting solid dissolved in EtOAc (5 mL), washed with water (3 mL) and concentrated in vacuo to give the title compound (62 mg, 98%), a mixture of geometrical isomers, as an oily solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additiontreated with toluene (2 mL)
  3. concentrationconcentrated in vacuo
  4. dissolutionthe resulting solid dissolved in EtOAc (5 mL)
  5. washwashed with water (3 mL)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98cf568bf3cd40a59f55844de824211d
Source dataset
uspto-grants-2004_09
Patent number
US06787541B1

Reaction notes

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