1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 14346817, compound

HRID 2051108Notes

Reaction equation

HRID 2051108 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:15]([CH3:16])=[N:14][N:13]=[N:12]1)(=[O:4])=[O:3].[CH3:17][O:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([N:27]([CH3:37])[C:28](=O)[O:29]C2C=CC=CC=2)[N:20]=1.C1CCN2C(=NCCC2)CC1>C(#N)C.O.C(OCC)C>[CH3:26][O:25][C:23]1[N:24]=[C:19]([O:18][CH3:17])[N:20]=[C:21]([N:27]([C:28]([NH:1][S:2]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:11]2[C:15]([CH3:16])=[N:14][N:13]=[N:12]2)(=[O:4])=[O:3])=[O:29])[CH3:37])[N:22]=1

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14179827HCID 14179827, compound2×HCID 14346816HCID 14346816, compound

Product 1

HCID 14346817HCID 14346817, compoundYield 79.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To 0.22 g of 2-(5-methyl-1H-tetrazol-1-yl)benzenesulfonamide (compound of Example 2, 0.32 g) and 0.32 g of phenyl (4,6-dimethoxy-1,3,5-triazin-2-yl)(methyl)carbamate in 4 ml of dry acetonitrile was added at room temperature 0.2 ml of DBU. The reaction mixture was allowed to stand for four days, then diluted with 4 ml of water, several ice chips and 4 ml of diethyl ether. After stirring this solution for one minute, the ether layer was removed by pipet and the remaining mixture was acidified by dropwise addition of 1N HCl. The resulting precipitate was filtered, washed with water and dried to give 0.32 g of a white solid, m.p. 180°-182° C. (d).

Workup

  1. customthe ether layer was removed by pipet
  2. additionthe remaining mixture was acidified by dropwise addition of 1N HCl
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c9253f9c5e6d443ca52191362497aeac
Source dataset
uspto-grants-1991_05
Patent number
US05017214

Reaction notes

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