Hydrochloric Acid → N-[(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-[(2-oxotetrahydro-3-furanylidene)methyl]benzenesulfonamide

HRID 1788877Notes

Reaction equation

HRID 1788877 reaction equation
[O:1]=[C:2]1[C:6](=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([NH2:17])(=[O:16])=[O:15])[CH2:5][CH2:4][O:3]1.[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([NH:28][C:29](=O)[O:30]C2C=CC=CC=2)[N:21]=1.N12CCCN=C1CCCCC2.Cl>C(#N)C.O>[CH3:27][O:26][C:24]1[CH:25]=[C:20]([O:19][CH3:18])[N:21]=[C:22]([NH:28][C:29]([NH:17][S:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[C:6]2[CH2:5][CH2:4][O:3][C:2]2=[O:1])(=[O:15])=[O:16])=[O:30])[N:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 542235172-[(2-Oxotetrahydro-3-furanylidene)methyl] benzenesulfonamide

Product 1

HCID 54353573N-[(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-[(2-oxotetrahydro-3-furanylidene)methyl]benzenesulfonamideYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 0.09 g (0.0004 mol) of the product of Example 3 and 0.15 g (0.0005 mol) of (4,6-dimethoxy-2-pyrimidinyl)carbamic acid, phenyl ester in 1 mL dry acetonitrile under nitrogen was added dropwise 0.08 mL (0.08 g, 0.0005 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture was stirred at room temperature for 30 min and was then diluted with water and acidified with 1N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and washed well with water and ether to yield 0.1 g (64%) of the title compound: m.p. 185°-190° (gas evolution); IR (nujol) 3180 (br), 1755, 1740, 1710, 1700, 1610, 1560, 1355, 1165 cm-1 ; NMR (CDCl3, 200 MHz) δ 3.05 (2H, m), 4.29 (2H, t, J=7 Hz), 3.99 (6H, s), 5.83 (1H, s), 7.2 (NH, s), 7.4-7.8 (3H, m), 8.1 (1H, m), 8.12 (NH, s), 8.14 (1H, m).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed well with water and ether

Sources & evidence

ORD record
ord-248ffe0971b44f2582d70db20b332f12
Source dataset
uspto-grants-1987_08
Patent number
US04685955

Reaction notes

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