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

HRID 1788878Notes

Reaction equation

HRID 1788878 reaction equation
[Cl:1][C:2]1[C:3]([CH:12]=[C:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([NH:29][C:30](=O)[O:31]C2C=CC=CC=2)[N:22]=1.N12CCCN=C1CCCCC2.Cl>C(#N)C.O>[Cl:1][C:2]1[C:3]([CH:12]=[C:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[C:4]([S:8]([NH:11][C:30]([NH:29][C:23]2[N:22]=[C:21]([O:20][CH3:19])[CH:26]=[C:25]([O:27][CH3:28])[N:24]=2)=[O:31])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=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 53966879HCID 53966879, compound

Product 1

HCID 543779873-Chloro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[(2-oxotetrahydro-3-furanylidene)methyl]benzenesulfonamideYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 0.15 g (0.0005 mol) of the product of Example 7 and 0.21 g (0.0008 mol) of (4,6-dimethoxy-2-pyrimidinyl)carbamic acid, phenyl ester in 1 mL dry acetonitrile under nitrogen was added dropwise 0.12 mL (0.12 g, 0.0008 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture was stirred at room temperature for 1 hour 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 0.2 g (83%) of the title compound: m.p. 212°-216° (dec); IR (nujol) 3410, 1765, 1730, 1605, 1365, 1340, 1155 cm-1 ; NMR (CDCl3, 200 MHz) δ 2.7-2.8 (2H, m), 3.94 (6H, s), 4.1-4.2 (2H, m), 5.84 (1H, s), 7.2-7.8 (3H, m), 8.25 (1H, m).

Workup

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

Sources & evidence

ORD record
ord-ce37ff459f5848f19fc1dbc7eb1ac0e2
Source dataset
uspto-grants-1987_08
Patent number
US04685955

Reaction notes

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