Ethyl chloroformate → Tris(2-carbethoxyaminoethyl)amine

HRID 257147ノート

反応式

HRID 257147 の反応式
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[NH2:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15][NH2:16])[CH2:11][CH2:12][NH2:13].[OH-:17].[K+]>C1C=CC=CC=1.O>[C:4]([NH:7][CH2:8][CH2:9][N:10]([CH2:14][CH2:15][NH:16][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:11][CH2:12][NH:13][C:4]([O:3][CH2:1][CH3:2])=[O:17])([O:3][CH2:1][CH3:2])=[O:5]

参加物

6

反応物 3

HCID 10928Ethyl chloroformate2 回HCID 14797Potassium HydroxideHCID 77731Tris(2-aminoethyl)amine

生成物 1

HCID 19784622Tris(2-carbethoxyaminoethyl)amine収率 85%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒2 回

反応条件

温度
5 °C

実験手順

In accord with the procedure of H. Schmidt et al., Z. anoro. allq. Chem., 578, 75 (1989), ethylchloroformate (33.4 g, 0.310 mol) was added dropwise to a solution of tris(2-aminoethyl)amine (TREN) (29.2 g, 0.20 mol) dissolved in a mixture of benzene (225 mL) and water (100 mL) cooled to 5° C. After the addition was completed, KOH (36.4 g, 0.650 mol) dissolved in water (35 mL) was added dropwise simultaneously with more ethylchloroformate (33.4 g, 0.310 mol). The reaction mixture was stirred for 2 hr. at 5° C. and then for 8 hr. at room temperature. The benzene layer was separated and the water layer extracted with chloroform (2×100 mL). The combined organic fractions were dried over MgSO4, decanted and the decantate evaporated to dryness to give the intermediate tris(2-carbethoxyaminoethyl)amine (5) in 85% yield as a thick oil which was used in subsequent reactions without further purification (1H NMR (CDCl3)δ1.27 (9H, t, 3JHH =7.1 Hz), δ2.60 (6H, t, 3JHH =5.7 Hz), δ3.23 (6H, br), δ4.10 (6H, q, 3J=7.1 5.50 (3H, br); IR 3300, 1720, 1530, 1250 cm-1).

後処理

  1. additionAfter the addition
  2. waitat 5° C. and then for 8 hr
  3. customat room temperature
  4. customThe benzene layer was separated
  5. extractionthe water layer extracted with chloroform (2×100 mL)
  6. dry with materialThe combined organic fractions were dried over MgSO4
  7. customdecanted
  8. customthe decantate evaporated to dryness

出典と根拠

ORDレコード
ord-b340bf4b24584c4cb0124093d080d9f6
出典データセット
uspto-grants-1993_11
特許番号
US05260436

反応ノート

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