Ethanol → HCID 135996309, compound

HRID 441296Notes

Reaction equation

HRID 441296 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[C:15]([S:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=[CH:13][C:12]=2[O:22][CH2:23][CH2:24][CH3:25])[NH:5][C:6](=[O:10])[C:7]=1[N:8]=O.C(O)C.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[C:15]([S:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH:14]=[CH:13][C:12]=2[O:22][CH2:23][CH2:24][CH3:25])[NH:5][C:6](=[O:10])[C:7]=1[NH2:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 24489Sodium DithioniteHCID 136017509HCID 136017509, compound

Product 1

HCID 135996309HCID 135996309, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Amino-5-nitroso-2-(2-propoxy-5-t-butylthiophenyl)-pyrimid-6-one (6.5 g.) (see Reference Example 7) was dissolved in boiling ethanol (150 ml.), and the solution was added all at once to a solution of sodium dithionite (26 g.) in water (150 ml.) at 80° C. The mixture immediately turned yellow. After 2 minutes, the mixture was cooled to room temperature and diluted with water (700 ml.), and then it was left to stand in an ice bath for 1 hour. The solid formed [4,5-diamino-2-(2-propoxy-5-t-butylthiophenyl)-pyrimid-6-one] was filtered off and washed with water. This material was used immediately for the next stage of the synthesis, because darkening occurred on standing.

Workup

  1. waitit was left
  2. waitto stand in an ice bath for 1 hour

Sources & evidence

ORD record
ord-b74e077553f04b55a1d47620d046d6c7
Source dataset
uspto-grants-1977_08
Patent number
US04039544

Reaction notes

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