Sodium hydride → HCID 178420294, compound

HRID 1358244

Reaction equation

HRID 1358244 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

6

Reactant 4

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

Product 1

HCID 178420294HCID 178420294, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 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.

Workup

  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.

Sources & evidence

ORD record
ord-0cb599674742428c9c869622561ad0b1
Source dataset
uspto-grants-2003_07
Patent number
US06596727B1

Linked notes

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