Hydroxylamine → HCID 59556680, compound

HRID 1172953Notes

Reaction equation

HRID 1172953 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C@H:11]1[CH2:15][CH2:14][O:13][CH2:12]1)[C:5]#[N:6].[NH2:16][OH:17]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C@H:11]1[CH2:15][CH2:14][O:13][CH2:12]1)/[C:5](=[N:16]/[OH:17])/[NH2:6]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 59556751HCID 59556751, compound

Product 1

HCID 59556680HCID 59556680, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under an atmosphere of nitrogen, (S)-3-chloro-4-(tetrahydrofuran-3-yloxy)benzonitrile (11.2 g, 50.1 mmol) and 50% aqueous hydroxylamine (3.31 g, 50.1 mmol) in EtOH (150.0 mL) was heated at 60° C. for 18 hr. Solvents removed in vacuo and the residue was azeotroped with MeOH. The residual solid was purified by precipitation from an ethyl acetate/30-60° C. pet/ether mixture (1:2) to give (S,Z)-3-chloro-N′-hydroxy-4-(tetrahydrofuran-3-yloxy)benzimidamide (5.3 g) LCMS (Table 1, Method b) Rt=1.52 min, m/z 257.09 (M+H)+.

Workup

  1. customSolvents removed in vacuo
  2. customthe residue was azeotroped with MeOH
  3. customThe residual solid was purified by precipitation from an ethyl acetate/30-60° C. pet/ether mixture (1:2)

Sources & evidence

ORD record
ord-79772434eef54b63be52931e1af2fc2b
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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