Sodium Dithionite → HCID 57883120, compound

HRID 1507617Notes

Reaction equation

HRID 1507617 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[N:10]([CH2:22][CH2:23][CH3:24])[C:11](=[O:21])[N:12]([CH:18]3[CH2:20][CH2:19]3)[C:13](=[O:17])[C:14]=2[N:15]=O)=O)=[CH:4][N:3]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CS(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[NH:15][C:14]3[C:13](=[O:17])[N:12]([CH:18]4[CH2:20][CH2:19]4)[C:11](=[O:21])[N:10]([CH2:22][CH2:23][CH3:24])[C:9]=3[N:8]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 86704347HCID 86704347, compound

Product 1

HCID 57883120HCID 57883120, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6-Chloro-N-(1-cyclopropyl-5-nitroso-2,6-dioxo-3-propyl-1,2,3,6-tetrahydro-pyrimidin-4-yl)-nicotinamide (8.2 g, 21.71 mmol, 1 eq) in 60 ml of DMSO was added Na2S2O4 (15.11 g, 86.84 mmol, 4 eq). The mixture was stirred at 90° C. for 3 hours. The mixture was quenched with water (50 ml). The resulting precipitate was obtained by filtration and washed with water to give the desired product (5.78 g, 77%) after vacuum dried overnight at 40° C.: 1H NMR (400 MHz, DMSO-d6) δ 14.1 (1H), 9.08 (1H), 8.48 (1H), 7.7 (1H), 4.00 (2H), 2.62 (1H), 1.78 (2H), 1.14 (2H), 0.92 (3H), 0.75 (2H); m/z (ES+) 346.79

Workup

  1. customThe mixture was quenched with water (50 ml)
  2. customThe resulting precipitate was obtained by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-de7e757ab1944b1e8c7bacf85a059d17
Source dataset
uspto-grants-2015_12
Patent number
US09221821B2

Reaction notes

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