1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19821176, compound

HRID 1030008Notes

Reaction equation

HRID 1030008 reaction equation
[S:1](=[O:15])(=[O:14])([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH2:12][CH3:13])[NH2:2].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([NH:26][C:27](=O)[O:28]C2C=CC=CC=2)[N:19]=1.N12CCCN=C1CCCCC2>C(#N)C>[CH3:25][O:24][C:22]1[CH:23]=[C:18]([O:17][CH3:16])[N:19]=[C:20]([NH:26][C:27](=[O:28])[NH:2][S:1]([O:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:10][CH2:11][CH2:12][CH3:13])(=[O:14])=[O:15])[N:21]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 19821175HCID 19821175, compound

Product 1

HCID 19821176HCID 19821176, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.74 g (0.008 mol) of 2-propoxyphenyl sulfamate are added at room temperature to 2.32 g (0.0084 mol) of phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate, dissolved in 100 ml of acetonitrile. After 1.33 g (0.0088 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) have been added, the reaction mixture is stirred at room temperature for 18 hours, concentrated, diluted with H2O and acidified using 2N hydrochloric acid to give a pH of 3-4. After the solids have been filtered off with suction and dried, 2.85 g (86% of theory) of 3-(4,6-dimethoxypyrimidin-2-yl)- 1-(2-propoxyphenoxysulfonyl)urea of melting point 108°-109° C. are obtained.

Workup

  1. concentrationconcentrated
  2. additiondiluted with H2O
  3. customto give a pH of 3-4
  4. filtrationAfter the solids have been filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-d7d56018c2c749ff9d8564293e471af1
Source dataset
uspto-grants-1992_04
Patent number
US05104443

Reaction notes

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