Dabco → 2-Chloro-N-[(5-cyano-2,6-dimethylpyrimidin-4-yl)-aminocarbonyl]benzenesulfonamide

HRID 4133

Reaction equation

HRID 4133 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]=[C:12]=[O:13])(=[O:10])=[O:9].[NH2:14][C:15]1[C:20]([C:21]#[N:22])=[C:19]([CH3:23])[N:18]=[C:17]([CH3:24])[N:16]=1.N12CCN(CC1)CC2>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]([NH:14][C:15]1[C:20]([C:21]#[N:22])=[C:19]([CH3:23])[N:18]=[C:17]([CH3:24])[N:16]=1)=[O:13])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 9237DabcoHCID 174071Benzenesulfonyl isocyanate, 2-chloro-HCID 27938634-Amino-5-cyano-2,6-dimethylpyrimidine

Product 1

HCID 140502052-Chloro-N-[(5-cyano-2,6-dimethylpyrimidin-4-yl)-aminocarbonyl]benzenesulfonamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.35 g of 2-Chlorobenzenesulfonyl isocyanate was dissolved in 10 ml xylenes and 25 ml methylene chloride. To this was added 2.96 g of 4-amino-2,6-dimethyl-5-pyrimidine carbonitrile and a catalytic amount of 1,4-diazabicyclo-[2.2.2]octane. The reaction was stirred under a CaSO4 drying tube for three days. The reaction was filtered to remove unreacted pyrimidine, and then the desired product was precipitated by addition of 1-chlorobutane, filtered off, rinsed well with 1-chlorobutane and dried in vacuo giving 5.2 g of the desired product, m.p. 125°-127°. IR: 2240 cm-1 (C≡N), 1730 cm-1 (C=O); NMR (DMSO-d6)δ: 2.6 (s, 6H), 7.4-8.1 (m, 4H) ppm indicating the title compound.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove unreacted pyrimidine
  3. customthe desired product was precipitated by addition of 1-chlorobutane
  4. filtrationfiltered off
  5. washrinsed well with 1-chlorobutane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c4afe691e3a7425cae2c519da2b6103e
Source dataset
uspto-grants-1988_02
Patent number
US04723991

Linked notes

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