Sodium hydride → HCID 178420294, 화합물

HRID 1358244

반응식

HRID 1358244 반응식
[H-].[Na+].[C:3]1([C@@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:17]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[N:20]=[CH:19][N:18]=1.[NH4+].[Cl-]>C1COCC1>[C:3]1([C@@H:9]2[CH2:10][CH2:11][C@H:12]([O:15][C:17]3[C:26]4[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=4[N:20]=[CH:19][N:18]=3)[CH2:13][CH2:14]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 125829694-Chloro-5,6,7,8-tetrahydroquinazolineHCID 178521547HCID 178521547, 화합물

생성물 1

HCID 178420294HCID 178420294, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
50 °C

실험 절차

0.5 g (16.7 mmol) of 80% NaH was added in portions to a solution of 1.85 g (105 mmol) of cis-4-phenylcyclohexanol in 30 ml of absolute THF. After this, the mixture was heated for 1 hour at 50° C., and 1.5 g (8.75 mmol) of 4-chloro-5,6,7,8-tetrahydroquinazoline, dissolved in 15 ml of absolute THF, were added dropwise. The reaction mixture was subsequently refluxed for 2 hours. After the mixture has cooled to room temperature, it was poured into saturated NH4Cl solution and this was extracted with ether, and the combined organic phase was dried over MgSO4. The solvent was evaporated in vacuo, and the residue (2.7 g) was purified by flash chromatography over silica gel, using n-hexane/ethyl acetate (2:1). Concentration gave 1.5 g (50.2% of theory), colorless crystals, m.p. 109° C.

후처리

  1. additionwere added dropwise
  2. temperatureThe reaction mixture was subsequently refluxed for 2 hours
  3. temperatureAfter the mixture has cooled to room temperature
  4. extractionthis was extracted with ether
  5. dry with materialthe combined organic phase was dried over MgSO4
  6. customThe solvent was evaporated in vacuo
  7. customthe residue (2.7 g) was purified by flash chromatography over silica gel
  8. concentrationConcentration
  9. customgave 1.5 g (50.2% of theory), colorless crystals, m.p. 109° C.

출처 및 근거

ORD 기록
ord-0cb599674742428c9c869622561ad0b1
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596727B1

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