Thiazolidinedione → 5-[3-(Phenylmethoxy)phenylmethyl-ene]-2,4-thiazolidinedione

HRID 1728320노트

반응식

HRID 1728320 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:17]1[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23].N1CCCCC1>N1C=CC=CC=1>[C:2]1([CH2:1][O:8][C:9]2[CH:10]=[C:11]([CH:12]=[C:21]3[S:17][C:18](=[O:23])[NH:19][C:20]3=[O:22])[CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 743423-Benzyloxybenzaldehyde

생성물 1

HCID 12494175-[3-(Phenylmethoxy)phenylmethyl-ene]-2,4-thiazolidinedione수율 100%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of 3-benzyloxybenzaldehyde (42.45 g, 200 mmol), 2,4-thiazolidinedione (23.43 g, 200.0 mmol), and piperidine (2 g) in 150 ml pyridine was refluxed for 16 h. The mixture was concentrated in vacuo, and the residue was triturated with 500 ml hot benzene, filtered, and the filtrate left standing at room temperature for two days. The resulting crystals were collected by filtration, washed with petroleum ether, and dried to give the product in 100% yield; mp 233-235° C.; IR (nujol): 1741, 1688 (CO) cm-1 ; NMR (DMSOd6TMS): δ5.19 (s, 2H, ArCH2), 7.15-7.25 (m, 3H), 7.3-7.5 (m, 6H), 7.73 (s, 1H, C=CH); Anal calcd for C17H13NO3, MW 311.36: C, 65.58; H, 4.21; N, 4.50; S, 10.30. Found: C, 65.53; H, 3.91; N, 4.52; S, 10.30. Mass spec m/e 312(M+1).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was triturated with 500 ml hot benzene
  3. filtrationfiltered
  4. waitthe filtrate left
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with petroleum ether
  7. customdried
  8. customto give the product in 100% yield

출처 및 근거

ORD 기록
ord-b07df93b035f47fb8f7171a8c9c1051f
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05326770

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