反応 #4233

反応方程式

sulfonyl isocyanate

2-(chloromethyl)benzenesulfonyl isocyanate

phosgene

2-amino-4,6-dimethoxypyrimidine

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

→

white solid

収率 69.6%

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

収率 69.6%

溶媒

acetonitrile

xylene

反応条件

後処理

1. 1
   温度at reflux
2. 2
   温度After 2.0 hrs at reflux
3. 3
   その他decanted
4. 4
   その他volatiles were removed
5. 5
   その他to give 1.56 g of crude product
6. 6
   ろ過Filtration

実験手順

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).

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