Sodium hydride → HCID 21906696, compound

HRID 1247598Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([C:8]([Cl:11])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[H-].[Na+].[SH:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21]>CN(C)C=O>[C:20]([O:19][C:18]([NH:17][CH2:16][CH2:15][S:14][C:2]1[CH:3]=[C:4]([C:8]([Cl:11])=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6])=[O:24])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2,5-dichloroisonicotinic acid (1.82 g) in anhydrous N,N-dimethylformamide (10 ml) was added 60% sodium hydride (0.455 g) in small portions. After gas evolution had ceased tert-butyl 2-mercaptoethylcarbamate (1.60 ml) was added. The reaction mixture was then heated at 60° C. under nitrogen for 10 hours. Further amounts of 60% sodium hydride (0.225 g) and tert-butyl 2-mercaptoethylcarbamate (1.60 ml) were then added and heating was continued for 2 hours. The reaction mixture was concentrated and the residue suspended in 2M aqueous hydrochloric acid (25 ml) and extracted into ethyl acetate (3×25 ml). The combined extracts were dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate:acetic acid (6:4:0.1) to afford the sub-titled compound (1.0 g) as a colourless powder.

Workup

additionwas added
temperatureheating
concentrationThe reaction mixture was concentrated
extractionextracted into ethyl acetate (3×25 ml)
dry with materialThe combined extracts were dried over anhydrous sodium sulphate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by chromatography on silica gel eluting with iso-hexane:ethyl acetate:acetic acid (6:4:0.1)

Sources & evidence

ORD record: ord-3123e9a5fa6e4887869c721212398816
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129246B2

Reaction notes

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