4-Chlorophenyl Isocyanate → HCID 60161674, compound

HRID 1843302Notes

Reaction equation

HRID 1843302 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].C(N(CC)CC)C.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>O1CCCC1>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:31])[O:14][C:11]2[CH:12]=[C:13]3[C:8]([CH2:7][CH2:6][CH2:5][N:4]3[CH2:1][C:2]#[CH:3])=[CH:9][CH:10]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 86704185HCID 86704185, compound

Product 1

HCID 60161674HCID 60161674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 1-(prop-2-ynyl)-1,2,3,4-tetrahydroquinolin-7-ol (400 mg, 2.14 mM) and triethylamine (0.6 mL) in dry tetrahydrofuran (THF; 5 mL) was stirred for half an hour under nitrogen atmosphere at room temperature (35° C.). To the stirred reaction mixture, 4-chlorophenyl isocyanate (411 mg/ml, 3.21 mM) was added at once and then the reaction mixture was further stirred for 32 hours under N2 atmosphere at RT (35° C.). The reaction mixture was concentrated under vacuum and then was added distilled water (15 mL) followed by the extraction with ether (3×15 mL). The ether layer was dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was finally chromatographed using chlorophorm-hexane (1:19) to afford 10f as solid. Yield: 520 mg, 71.42%.

Workup

  1. additionwas added at once and then the reaction mixture
  2. stirringwas further stirred for 32 hours under N2 atmosphere at RT (35° C.)
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionwas added
  5. distillationdistilled water (15 mL)
  6. extractionfollowed by the extraction with ether (3×15 mL)
  7. dry with materialThe ether layer was dried over sodium sulphate
  8. concentrationconcentrated under vacuum
  9. customto afford the crude product, which
  10. customwas finally chromatographed

Sources & evidence

ORD record
ord-81c41158adb7406399af38da166e26a2
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

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