Chlorosuccinimide → 4-Chloro-2-(pyridin-3-yl)-1,3-thiazol-5-amine hydrochloride

HRID 882000Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([NH2:12])=[CH:10][N:11]=2)[CH:2]=1.[Cl:13]N1C(=O)CCC1=O>O1CCOCC1>[ClH:13].[Cl:13][C:10]1[N:11]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[S:8][C:9]=1[NH2:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a dry 250 ml round bottom flask equipped with magnetic stirrer, was charged 6.3 g (35.5 mmoles) of 2-(pyridin-3-yl)-1,3-thiazol-5-amine, and 100 mLs of anhydrous 1,4-dioxane. The solution was cooled to ˜0° C. and 4.75 g (35.5 mmoles) of N-chlorosuccinimide was added portionwise at a rate that maintained the temperature below 10° C. The reaction mixture was stirred at 5-10° C. for 20 minutes, and then filtered through a small pad of diatomaceous earth. The filtrate was diluted with 50 mLs of diethyl ether, and acidified with 10 mLs of 4.0 M HCl in 1,4-dioxane. The resulting solid was collected by vacuum filtration, washed with ethyl ether (100 mLs) and methylene chloride (500 mLs), and then dried in vacuuo at 40° C. to afford 7.5 g (85%) of an orange solid: 1H NMR (400 MHz, DMSO-d6) δ 9.08 (d, J=2.1 Hz, 1H), 8.76 (dt, J=9.5, 4.7 Hz, 1H), 8.66 (ddd, J=8.3, 2.0, 1.3 Hz, 1H), 7.97 (dt, J=15.6, 7.8 Hz, 1H).

Workup

customTo a dry 250 ml round bottom flask equipped with magnetic stirrer
temperaturemaintained the temperature below 10° C
filtrationfiltered through a small pad of diatomaceous earth
additionThe filtrate was diluted with 50 mLs of diethyl ether
filtrationThe resulting solid was collected by vacuum filtration
washwashed with ethyl ether (100 mLs) and methylene chloride (500 mLs)
customdried in vacuuo at 40° C.

Sources & evidence

ORD record: ord-31f5f11fc0d344239de924f386f8d688
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993769B2

Reaction notes

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