2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → HCID 70274702, compound

HRID 867948Notes

Reaction equation

O([C:8]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:9][N+:10]([O-:12])=[O:11])C1C=CC=CC=1.[NH2:20][CH2:21][CH2:22][S:23][CH2:24][C:25]1[N:26]=[C:27]([CH2:30][N:31]([CH3:33])[CH3:32])[S:28][CH:29]=1>O1CCCC1.C(O)(C)C>[CH3:33][N:31]([CH2:30][C:27]1[S:28][CH:29]=[C:25]([CH2:24][S:23][CH2:22][CH2:21][NH:20][C:8]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][N+:10]([O-:12])=[O:11])[N:26]=1)[CH3:32]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 7.07 g (27.5 mmol) of 1,1-diphenoxy-2-nitroethene in 70 ml of tetrahydrofuran was stirred at 25° C. To this solution was added a mixture of 6.83 g (27.5 mmol) of 93% pure 4-[[(2-aminoethyl)thio]methyl]-N,N-dimethyl-2-thiazolemethanamine in 100 ml of isopropyl alcohol. The reaction mixture was stirred for approximately one hour at 25° C. and the progress of the reaction was followed by thin-layer chromatography to provide N-[2-[[[2-[(dimethylamino)methyl]-4-thiazolyl]methyl]thio]ethyl]-2-nitro-1-phenoxy-1-etheneamine. The product was not isolated but rather used directly in the following reaction.

Workup

additionTo this solution was added

Sources & evidence

ORD record: ord-13efd678ac30484584b2a797a97fbfc6
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04777260

Reaction notes

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