Sodium Hydroxide → HCID 178425948, compound

HRID 638234Notes

Reaction equation

[OH-].[Na+].[F:3][C:4]1([F:27])[O:25][C:8]2=[CH:9][C:10]3[N:14]=[C:13]([S:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=4)[NH:12][C:11]=3[CH:24]=[C:7]2[O:6][CH:5]1[F:26].Cl[O-].[Na+].S(S([O-])=O)([O-])=[O:32].[Na+].[Na+].P([O-])(O)(O)=O.[Na+]>O1CCOCC1.O>[F:27][C:4]1([F:3])[O:25][C:8]2=[CH:9][C:10]3[N:14]=[C:13]([S:15]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=4)=[O:32])[NH:12][C:11]=3[CH:24]=[C:7]2[O:6][CH:5]1[F:26]

Participants

Conditions

Temperature: 30 °C

Procedure

2.4 ml of 2M sodium hydroxide solution and 0.8 ml of water are added to a solution of 1.75 g of 6,6,7-trifluoro-6,7-dihydro-2-[(5-methyl-2-pyridyl)methylthio]-1H-[1,4]-dioxino[2,3-f]benzimidazole in 18 ml of dioxane. A mixture of 4.6 ml of sodium hypochlorite solution (8.9 g of active chlorine per ml) and 2.9 ml of 2M sodium hydroxide solution is added to the above solution at 30° C. in the course of 15 min. The mixture is stirred at 30° C. for 50 min., some drops of 2M sodium dithionite solution are added and the solution is concentrated in vacuo. 100 ml of water and 20 ml of ethyl acetate are added to the residue, and the title compound (1.6 g, 87% yield of m.p. 186°-187° C.) is precipitated by addition of sodium dihydrogen phosphate solution up to pH 7.

Workup

additionis added to the above solution at 30° C. in the course of 15 min
concentrationthe solution is concentrated in vacuo
addition100 ml of water and 20 ml of ethyl acetate are added to the residue

Sources & evidence

ORD record: ord-94b70efb468447a39093f3b22600d7ed
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04560693

Reaction notes

Loading…