Sodium hydride → HCID 11574702, compound

HRID 1441939Notes

Reaction equation

HRID 1441939 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30]>CCOCC>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:29](=[O:30])[NH:28][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[Cl:21])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76833Chlorophenyl isocyanateHCID 68543194HCID 68543194, compound

Product 1

HCID 11574702HCID 11574702, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.239 g., 1 mmol) in dry ether (10 ml) was added to a stirred suspension of sodium hydride (0.024 g., 1 mmol) in dry ether (15 ml) at −10° C. during 10 min. The reaction mixture was stirred for 20 min. Then 2-chlorophenyl isocyanate (0.184 g:, 1.2 mmol) was added to the stirring reaction mixture. Stirring was continued for additional 2 hours during which the temperature was allowed to rise to room temperature (35° C.). The reaction mixture was quenched with water (0.2 ml), concentrated under vaccum, diluted with water (5 ml), extracted with chloroform (2×5 ml) and dried over sodium sulphate. The combined fractions of chloroform were concentrated under vaccum. The residue was chromatographed on silica gel using chloroform: hexane (20:80) as eluant to give 2i; yield: 0.25 g. (63.7%).

Workup

  1. stirringStirring
  2. waitwas continued for additional 2 hours during which
  3. customto rise to room temperature
  4. custom(35° C.)
  5. customThe reaction mixture was quenched with water (0.2 ml)
  6. concentrationconcentrated under vaccum
  7. additiondiluted with water (5 ml)
  8. extractionextracted with chloroform (2×5 ml)
  9. dry with materialdried over sodium sulphate
  10. concentrationThe combined fractions of chloroform were concentrated under vaccum
  11. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-b2714d4eef924619a2272f00c779de8d
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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