Propanal → Bis(2-chloroethyl) 1-ureidopropylphosphonate

HRID 1415278

반응식

HRID 1415278 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

HCID 53932379Bis(2-chloroethyl) 1-ureidopropylphosphonate

실험 절차

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.

후처리

  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°

출처 및 근거

ORD 기록
ord-b4837eaba221418f979d57d9b60e02ba
출처 데이터셋
uspto-grants-1977_01
특허 번호
US04003965

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