Triethylamine → Nilutamide EP impurity A

HRID 839886Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

1 ml of triethylamine was added to a mixture of 49.6g of 3-trifluoromethyl-4-nitrophenyl isocyanate in 500 ml of tetrahydrofuran and then 18 g of 2-amino-2-cyanopropane were rapidly added thereto. The mixture was stirred for 72 hours at 20° C and was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 methylene chloride-acetone mixture to obtain 27 g of 1-(3'-trifluoromethyl-4'-nitrophenyl)-4,4 -dimethyl-5-imino-imidazoline-2-one melting at 168° C.

Workup

customwas evaporated to dryness under reduced pressure
customThe residue was chromatographed over silica gel
washwas eluted with an 8-2 methylene chloride-acetone mixture

Sources & evidence

ORD record: ord-b6759348af99474982db55428dfd6a57
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04097578

Reaction notes

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