Hydrochloric Acid → 2-Cyano-2-[4-(2,5-dichloro-phenoxy)-3-fluoro-phenylthiocarbamoyl]-acetamide

HRID 33761

Reaction equation

CC(C)([O-])C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[Cl:13][C:14]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[S:25])=[CH:19][C:18]=1[F:26].Cl>C1COCC1>[C:7]([CH:9]([C:24](=[S:25])[NH:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:15]2[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:14]=2[Cl:13])=[C:18]([F:26])[CH:19]=1)[C:10]([NH2:12])=[O:11])#[N:8]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of potassium tert-butoxide (0.6 g, 5.36 mmol) in 10 ml of anhydrous THF was added 2-cyanoacetamide (0.45 g, 5.36 mmol) under argon. The mixture was cooled to 5° C. and added dropwise to a solution of 4-(2,5-dichloro-phenoxy)-3-fluoro-phenylisothiocyanate (1.53 g, 4.87 mmol) in 5 ml of dry THF with stirring under argon. After 15 min of stirring at 5° C., this reaction mixture was warmed to room temperature and stirred for another 2 h. The reaction mixture was poured into 200 ml of ice water with stirring and acidified with 10% HCl. The solid was filtered and washed with water. After drying in vacuo, the crude product (1.6 g, 82.5%) was obtained in sufficient purity for the next step.

Workup

stirringAfter 15 min of stirring at 5° C.
temperaturethis reaction mixture was warmed to room temperature
stirringstirred for another 2 h
stirringwith stirring
filtrationThe solid was filtered
washwashed with water
customAfter drying in vacuo

Sources & evidence

ORD record: ord-119a1caf42714a83a6e34387060e5fcd
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429667B2

Linked notes

Loading…