Reacción #4233

Ecuación de reacción

sulfonyl isocyanate

2-(chloromethyl)benzenesulfonyl isocyanate

phosgene

2-amino-4,6-dimethoxypyrimidine

2-(chloromethyl)-N-(butylaminocarbonyl)benzene sulfonamide

→

white solid

Rendimiento 69.6%

2-(Chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Rendimiento 69.6%

Disolventes

acetonitrile

xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux
2. 2
   TemperaturaAfter 2.0 hrs at reflux
3. 3
   Otrodecanted
4. 4
   Otrovolatiles were removed
5. 5
   Otroto give 1.56 g of crude product
6. 6
   FiltraciónFiltration

Procedimiento

A solution of 2-(chloromethyl)-N-(butylaminocarbonyl)benzene sulfonamide (1.33 g, 4.38 mmol) and diazabicyclo[2.2.2]octane (5 mg) in xylene (12 ml) was heated at reflux and contacted in portions with phosgene (1.0 ml. condensed phase). After 2.0 hrs at reflux, the mixture was cooled to room temperature, decanted, and volatiles were removed to give 1.56 g of crude product. The IR spectrum of 2-(chloromethyl)benzenesulfonyl isocyanate featured a strong band at 2250 cm-1. The crude sulfonyl isocyanate was contacted with acetonitrile (10 ml) and 2-amino-4,6-dimethoxypyrimidine (0.68 g, 4.4 mmol) and stirred for 16 hrs. Filtration gave 1.18 g of white solid, mp 192°-193°. The sample was dissolved in 0.5N NaOH, filtered and pH adjusted to 6.5. The mixture was cooled and filtered and the solid washed with ice water and dried to give 0.90 g of white solid. 1H nmr δDMSO-d6TMS 12.7 (brd s, 10.50 (s, 1H) 8.13-7.97 (m, 1H), 7.73-7.40 (m, 3H), 5.90 (s, 1H), 5.10 (s, 2H), 3.87 (s, 6H).

Fuente