Triethylamine → (6-Trifluoromethyl-7-(2(-4-chlorophenoxy)ethoxy)-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl]methanephosphonic acid diethyl ester

HRID 368965노트

반응식

HRID 368965 반응식
[CH2:1]([O:3][P:4]([CH2:9][NH:10][C:11]1[CH:16]=[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[C:14]([C:28]([F:31])([F:30])[F:29])=[CH:13][C:12]=1[NH2:32])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C(N(CC)CC)C.[Cl-].C([O:43][C:44](=O)[C:45](O)=[O:46])C.Cl.C([NH+](CC)CC)C>O1CCCC1>[CH2:6]([O:5][P:4]([CH2:9][N:10]1[C:11]2[C:12](=[CH:13][C:14]([C:28]([F:30])([F:31])[F:29])=[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH:16]=2)[NH:32][C:44](=[O:43])[C:45]1=[O:46])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10994676N-[2-amino-4-trifluoromethyl-5-(2(-4-chlorophenoxy)ethoxy)phenyl]-aminomethanephosphonic acid diethyl esterHCID 21900368Triethylammonium hydrochlorideHCID 23618337Oxalic acid monoethylester chloride

생성물 1

HCID 15818832(6-Trifluoromethyl-7-(2(-4-chlorophenoxy)ethoxy)-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl]methanephosphonic acid diethyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2.5 g of N-[2-amino-4-trifluoromethyl-5-(2(-4-chlorophenoxy)ethoxy)phenyl]-aminomethanephosphonic acid diethyl ester is introduced in 60 ml of tetrahydrofuran with 733 mg of triethylamine and mixed drop by drop at room temperature with a solution of 719 mg (0.59 ml) of oxalic acid ethyl ester chloride in 15 ml of tetrahydrofuran. Then, it is stirred for 2 hours at room temperature. After triethylammonium hydrochloride is suctioned out, the filtrate is concentrated by evaporation. The residue is taken up in 25 ml of ethanol and 25 ml of 1N hydrochloric acid and heated for 2 hours to a bath temperature of 120° C. After the ethanol is distilled off, it is diluted with water to 50 ml, and extracted three times with 50 ml of ethyl acetate each. The ethyl acetate phase is washed with water, dried, filtered and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride:ethanol=10:1. 810 mg of [(6-trifluoromethyl-7-(2(-4-chlorophenoxy)ethoxy)-1,2,3,4-tetrahydro-2,3-dioxoquinoxalin-1-yl]methanephosphonic acid diethyl ester is obtained.

후처리

  1. concentrationthe filtrate is concentrated by evaporation
  2. temperature25 ml of 1N hydrochloric acid and heated for 2 hours to a bath temperature of 120° C
  3. distillationAfter the ethanol is distilled off
  4. additionit is diluted with water to 50 ml
  5. extractionextracted three times with 50 ml of ethyl acetate each
  6. washThe ethyl acetate phase is washed with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation
  10. customThe residue is chromatographed on silica gel with methylene chloride

출처 및 근거

ORD 기록
ord-e9fbf938b4964a42b7d5bbb5752a1333
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136805

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