Propanal → Bis(2-chloroethyl) 1-ureidopropylphosphonate

HRID 1415278

反応式

HRID 1415278 の反応式
[CH:1](=O)[CH2:2][CH3:3].[NH2:5][C:6]([NH2:8])=[O:7].[P:9]([O:18][CH2:19][CH2:20][Cl:21])([O:14][CH2:15][CH2:16][Cl:17])[O:10]CCCl>>[NH:5]([CH:1]([P:9](=[O:10])([O:14][CH2:15][CH2:16][Cl:17])[O:18][CH2:19][CH2:20][Cl:21])[CH2:2][CH3:3])[C:6]([NH2:8])=[O:7]

参加物

4

反応物 3

HCID 527PropanalHCID 1176UreaHCID 8783Tris(2-chloroethyl) phosphite

生成物 1

HCID 53932379Bis(2-chloroethyl) 1-ureidopropylphosphonate

実験手順

Freshly distilled propionaldehyde, 58.0g (1.0 mole), is added dropwise in 1 hr to a stirred mixture of 60.0g (1.0 mole) of powdered urea and 269.5g (1.0 mole) of crude tris (2-chloroethyl) phosphite at 105°-112° C. Heat of reaction keeps the temperature at this level without external warming during most of the aldehyde addition. The reaction mixture is warmed for 0.25 hr more, and then it is stripped to 122°/2mm, giving a viscous, yellow residue, crude bis(2-chloroethyl) 1-ureidopropylphosphonate. This is dissolved in 100ml of acetonitrile and 36g (2.0 moles) of water, and the solution is warmed at reflux for 1 hr. A solid forms during warming and is separated by filtration of the warm reaction mixture; and then it is stirred and warmed in more acetonitrile and water, and the mixture is filtered while warm to give 76.2g (42%) of white solid, mp 185°-186° dec. A 5.0-g portion is recrystallized from acetic acid-water to give 3.2g: mp 189°-191° dec; 31P nmr (CD3SOCD3) -23.0 ppm(m); 1H nmr δ 8.5 (broad, 4, OH and NH2), 6.2 (broad, 1, NH), 3.7 (broad, 1, CH), 1.6 and 0.9 (broad, 5, CH2CH3); acidity 2.01 equiv/mole, pK1 2.70, pK2 7.30.

後処理

  1. temperatureHeat of reaction
  2. temperaturewithout external warming during
  3. temperatureThe reaction mixture is warmed for 0.25 hr more
  4. customis stripped to 122°

出典と根拠

ORDレコード
ord-b4837eaba221418f979d57d9b60e02ba
出典データセット
uspto-grants-1977_01
特許番号
US04003965

関連ノート

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