Chloroacetamide → 1-(Carbamylmethyl)-5-iodo-2-(p-toluenesulfonamido)pyridine

HRID 1372486Notes

Reaction equation

[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:22][C:23]([NH2:25])=[O:24]>CN(C)C=O>[C:23]([CH2:22][N:6]1[CH:7]=[C:2]([I:1])[CH:3]=[CH:4][CH:5]1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(=[O:24])[NH2:25]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of the product (1.60 g, 4.27 mmol) from Step A in 8.0 mL of dry N,N-dimethylformamide was added sodium hydride (188 mg of 60 weight % dispersion in mineral oil, 4.44 mmol). After 15 min, the solution was warmed to 60° C. for 10 min, and was then cooled to room temperature. Chloroacetamide (420 mg) was added in one portion, and the solution was then warmed to 100° C. After 2.5 h, the solution was cooled to room temperature and poured into 70 mL of ice-water. The resultant precipitate was collected, washed with water and air-dried overnight. The crude product was subsequently stirred with 20 mL of methanol for several minutes, and the product was collected by filtration to afford the title compound as a white powder. LC/MS 414.9 (M+1-H2O).

Workup

temperaturewas then cooled to room temperature
temperaturethe solution was then warmed to 100° C
waitAfter 2.5 h
temperaturethe solution was cooled to room temperature
customThe resultant precipitate was collected
washwashed with water
customair-dried overnight
filtrationthe product was collected by filtration

Sources & evidence

ORD record: ord-2bed0e5fc6e041e9a6336238c2d53e81
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157490B2

Reaction notes

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