Sodium hydride → HCID 178420294, compound

HRID 1898888Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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 had 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. ##STR12##

Workup

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

Sources & evidence

ORD record: ord-03d1dba484164f70a713fba3ca4b65b4
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571815

Reaction notes

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