1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11016088, compound

HRID 2187342Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[CH:3]=[N:4][C:5]1[CH:6]=[CH:7][C:8]([C:15]([O:17][CH3:18])=[O:16])=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:10]=1.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([NH:30][C:31](OC2C=CC=CC=2)=[O:32])[N:23]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[CH3:29][O:28][C:26]1[CH:27]=[C:22]([O:21][CH3:20])[N:23]=[C:24]([NH:30][C:31]([NH:14][S:11]([C:9]2[CH:10]=[C:5]([N:4]=[CH:3][N:2]([CH3:19])[CH3:1])[CH:6]=[CH:7][C:8]=2[C:15]([O:17][CH3:18])=[O:16])(=[O:13])=[O:12])=[O:32])[N:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 1.50 g of 5-(2-dimethylamino-1-azaethenyl)-2-methoxycarbonylbenzenesulfonamide, 1.61 g of 4,6-dimethoxy-2-phenoxycarbonylaminopyrimidine, 32 ml of acetonitrile and 0.83 ml of DBU is stirred initially at 0° C. and then at room temperature until the reaction has ended. The reaction mixture is then concentrated under reduced pressure. The residue is taken up in water and washed with diethyl ether. The aqueous phase is carefully acidified with conc. hydrochloric acid (pH 6) and the sulfonylurea precipitate is separated off, washed with diisopropyl ether and water and dried. This affords 1.89 g of the desired sulfonylurea, melting point 73-75° C.;

Workup

customat room temperature
concentrationThe reaction mixture is then concentrated under reduced pressure
washwashed with diethyl ether
customthe sulfonylurea precipitate is separated off
washwashed with diisopropyl ether and water
customdried

Sources & evidence

ORD record: ord-6a4ad6ed00144a1396842a210de12e0f
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410482B1

Reaction notes

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