1,8-Diazabicyclo(5.4.0)undec-7-ene → N-Methoxy-2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzenecarboximidoyl chloride

HRID 982298Notes

Reaction equation

HRID 982298 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([Cl:15])=[N:12][O:13][CH3:14])(=[O:4])=[O:3].[CH3:16][O:17][C:18]1[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][C:26](=O)[O:27]C2C=CC=CC=2)[N:19]=1.C1CCN2C(=NCCC2)CC1>>[CH3:14][O:13][N:12]=[C:11]([Cl:15])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[S:2]([NH:1][C:26]([NH:25][C:20]1[N:19]=[C:18]([O:17][CH3:16])[N:23]=[C:22]([CH3:24])[N:21]=1)=[O:27])(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11448329Carbamic acid, (4-methoxy-6-methyl-1,3,5-triazin-2-yl)-, phenyl esterHCID 540187652-(Aminosulfonyl)-N-methoxybenzenecarboximidoyl chloride

Product 1

HCID 53974237N-Methoxy-2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzenecarboximidoyl chlorideYield 67.4%

Procedure

By the procedure of Example 5, 0.4 g of the product of Example 4 was reacted with 0.46 g of phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate and 0.25 g of DBU. The resulting suspension was acidified, without prior filtration, with concentrated hydrochloric acid and filtered. The residue was washed with excess water and suction-dried to yield 0.45 g of the subject compound, m.p. 182° to 184° C.

Workup

  1. filtrationwithout prior filtration
  2. filtrationwith concentrated hydrochloric acid and filtered
  3. washThe residue was washed with excess water
  4. customsuction-dried

Sources & evidence

ORD record
ord-7f50d50f781143d780017a64d5b70691
Source dataset
uspto-grants-1991_02
Patent number
US04995901

Reaction notes

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