Sodium Hydroxide → S-Nitrosocaptopril

HRID 1199351Notes

Reaction equation

HRID 1199351 reaction equation
[CH3:1][C@@H:2]([C:5]([N:7]1[C@H:11]([C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8]1)=[O:6])[CH2:3][SH:4].[N:15]([O-])=[O:16].[Na+].[OH-].[Na+]>Cl>[CH3:1][C@@H:2]([C:5]([N:7]1[C@H:11]([C:12]([OH:14])=[O:13])[CH2:10][CH2:9][CH2:8]1)=[O:6])[CH2:3][S:4][N:15]=[O:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 44093CaptoprilHCID 23668193Sodium Nitrite

Product 1

HCID 129596S-Nitrosocaptopril

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

50 mg of Captopril (0.236 mMoles) was dissolved in 10 ml of 0.1 M HCl at room temperature and cooled briefly in an ice bath. A total of 0.25 ml of 1 M NaNO2 was then added in several small portions with rapid swirling. After 2 min on ice, 1.0 ml of 0.5 M Na2HPO4 was added and the solution was adjusted to pH 7.3 with 0.1 M NaOH. The solution displayed absorption maxima at 542 nm (E=19.8 M-1 cm-1) and 330 nm (E=995 M-1 cm-1).

Workup

  1. temperaturecooled briefly in an ice bath
  2. customabsorption maxima at 542 nm (E=19.8 M-1 cm-1) and 330 nm (E=995 M-1 cm-1)

Sources & evidence

ORD record
ord-13d06335fb874e1e83d7f5a74d0a5141
Source dataset
uspto-grants-1990_02
Patent number
US04900719

Reaction notes

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