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Phosgene → HCID 11003433, 화합물

HRID 742092
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인쇄 미리보기

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HRID 742092 반응식
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[O:6]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:26])([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N1C=CN=N1.[C:32](Cl)(Cl)=[O:33]>C(N(CC)CC)C.C1(C)C=CC=CC=1>[N:1]1([C:32]([O:25][C:19]([CH3:26])([C:16]2[CH:17]=[CH:18][C:13]([O:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:14][CH:15]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:33])[CH:5]=[N:4][CH:3]=[N:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6371PhosgeneHCID 92571H-1,2,4-TriazoleHCID 10859095Ethyl 2-(4-phenoxyphenyl)lactateHCID 178418936HCID 178418936, 화합물

생성물 1

HCID 11003433HCID 11003433, 화합물수율 102.9%

시약·촉매·용매 2

HCID 1140Toluene용매
HCID 8471
Triethylamine
용매

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온도
103 °C

실험 절차

A mixture of 6.9 g of 1,2,4-triazole, 100 mL of toluene, 14.3 g of ethyl 2-(4phenoxyphenyl)lactate, and 20 g of triethylamine was heated to 103° C. to dissolve the triazole and then cooled to -60° C. Phosgene (6.4 g) was added at 57°-60° C. over 2.5 h. After holding the reaction mixture at 59°-60° C. for 1.25 h, the reaction mixture was cooled to -5° C. Ice (100 g) was added, and the temperature dropped to -8° C. The aqueous layer was separated and extracted one time with 15 mL of toluene. The organic layers were combined and washed with cold water (2 times with 25 mL), dried (MgSO4), filtered, and evaporated in vacuo to yield 19.6 g of the title compound as a viscous oil. 1H NMR (300 MHz, CDCl3): δ8.85 (s, 1H), 8.08 (s,1H), 7.59-7.00 (m, 11H), 4.25 (m,2H), 2.18 (s,3H), 1.23 (t,3H).

후처리

  1. temperaturecooled to -60° C
  2. customat 59°-60° C.
  3. customfor 1.25 h
  4. temperaturethe reaction mixture was cooled to -5° C
  5. additionthe temperature dropped to -8° C
  6. customThe aqueous layer was separated
  7. extractionextracted one time with 15 mL of toluene
  8. washwashed with cold water (2 times with 25 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-a71173dd1f1f4e23b635a9b145ddd388
출처 데이터셋
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05552554

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