Triethylamine → 5-Naphthalen-2-yl-2,3-dihydro-[1,3,4]oxadiazol-2-yl-cyanamide

HRID 1107895

반응식

HRID 1107895 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][NH2:14])=[O:12].C(N(CC)CC)C.C1C=CC(O[C:29](OC2C=CC=CC=2)=[N:30][C:31]#[N:32])=CC=1>C(O)(C)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[O:12][CH:29]([NH:30][C:31]#[N:32])[NH:14][N:13]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1234852-NaphthohydrazideHCID 688090Diphenyl N-Cyanocarbonimidate

생성물 1

HCID 187074915-Naphthalen-2-yl-2,3-dihydro-[1,3,4]oxadiazol-2-yl-cyanamide수율 51%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a stirred solution of naphthalene-2-carboxylic acid hydrazide (0.7 g, 3.76 mmol) in isopropanol (40 ml) was added triethylamine (630 μl, 4.51 mmol) and diphenyl cyanocarbonimidate (0.99 g, 4.14 mmol) and the resulting reaction mixture was stirred at room temperature for 1.5 h. The volatiles were evaporated in vacuo and to the residue was added water (50 ml) and diethyl ether (50 ml). The organic phase was separated and the aqueous phase was acidified to pH=1 with concentrated hydrochloric acid. The precipitate was filtered off and washed with water (3×10 ml) and diethyl ether (2×10 ml) and dried in vacuo at 50° C. which afforded 0.45 g (51%) of the title compound as a solid.

후처리

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo and to the residue
  3. additionwas added water (50 ml) and diethyl ether (50 ml)
  4. customThe organic phase was separated
  5. filtrationThe precipitate was filtered off
  6. washwashed with water (3×10 ml) and diethyl ether (2×10 ml)
  7. customdried in vacuo at 50° C. which

출처 및 근거

ORD 기록
ord-aa8283b3d06042a8930d331c4b2605d8
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06063800

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