Sodium hydride → HCID 11554399, compound

HRID 1441941Notes

Reaction equation

HRID 1441941 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][C:25]([N:28]=[C:29]=[O:30])=[CH:24][C:23]=1[C:31]([F:34])([F:33])[F:32]>O1CCCC1>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:29](=[O:30])[NH:28][C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[C:23]([C:31]([F:32])([F:33])[F:34])[CH:24]=3)=[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 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 68543194HCID 68543194, compound

Product 1

HCID 11554399HCID 11554399, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-1, 2, 3, 4-tetrahydro-quinolin-6-ol (0.239 g., 1 mmol) in dry tetrahydrofuran (5 ml) was added to a stirred suspension of sodium hydride (0.024 g., 1 mmol) in dry tetrahydrofuran (5 ml) at −10° C. during 5 min. The reaction mixture was stirred for 20 min. Then 4-chloro-3-trifluoromethyl-phenyl isocyanate (0.265 g., 1 mmol) was added to the stirring reaction mixture. Stirring was continued for additional 2.5 hours during which the temperature was allowed to rise to room temperature (34° 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 2k; yield: 0.25 g. (54.2%), m.p. 151° C., C24H20ClF3N2O2; 1H NMR δ ppm (CDCl3): 2.00 (bs, 2H), 2.79 (t, 2H), 3.36 (t, 2H), 4.46 (s, 2H), 6.42-6.46 (m, 1H), 6.70-6.79 (m, 2H), 6.96 (s, 1H), 7.23-7.31 (m, 5H), 7.75-7.82 (m, 2H); IR vmax (KBr) (cm−1): 555, 701, 898, 1027, 1218, 1362, 1509, 1635, 1721, 2375, 2658, 2957, 3028, 3449, 3756; MS: m/z=461 (M+).

Workup

  1. stirringStirring
  2. waitwas continued for additional 2.5 hours during which
  3. customto rise to room temperature
  4. custom(34° 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-af317c7d3e9f4eb9809c7ab84682cc6e
Source dataset
uspto-grants-2010_02
Patent number
US07655801B2

Reaction notes

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