Dabco → 2-(1-Cyclopentenyl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 1380477Notes

Reaction equation

HRID 1380477 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.C1N2CCN(CC2)C1.[C:19]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30]([N:33]=[C:34]=[O:35])(=[O:32])=[O:31])[CH2:23][CH2:22][CH2:21][CH:20]=1>C(Cl)Cl>[C:19]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30]([NH:33][C:34]([NH:1][C:2]2[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=2)=[O:35])(=[O:31])=[O:32])[CH2:23][CH2:22][CH2:21][CH:20]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 5872364-Methoxy-6-methylpyrimidin-2-amineHCID 130973822-(1-Cyclopentenyl)benzenesulfonyl Isocyanate

Product 1

HCID 130973832-(1-Cyclopentenyl)-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-amino-4-methoxy-6-methylpyrimidine (0.45 g, 3.2 mmol), methylene chloride and DABCO (ca. 10 mg) was contacted with 2-(1-cyclopentenyl)benzenesulfonyl isocyanate in methylene chloride solution at ambient temperature. After approximately 20 minutes the product crystallized from the reaction mixture and was collected by filtration and rinsed with ether. In this manner, 0.35 g of product was obtained, m.p. 235°-236°. The infrared spectrum exhibited a carbonyl absorption at 1710 cm-1 indicating the title compound.

Workup

  1. customAfter approximately 20 minutes the product crystallized from the reaction mixture
  2. filtrationwas collected by filtration
  3. washrinsed with ether

Sources & evidence

ORD record
ord-e812ab77431f43bc9b0305ce0f4ae817
Source dataset
uspto-grants-1986_04
Patent number
US04582525

Reaction notes

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