Ammonia → HCID 25096336, compound

HRID 1015427Notes

Reaction equation

HRID 1015427 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH2:20][CH2:21][CH2:22][NH:23]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(C1NC=CN=1)(C1NC=CN=1)=[S:29].C([N:42]([CH2:45]C)CC)C.N>C1COCC1.CO>[C:1]1([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:19]=2[CH2:20][CH2:21][CH2:22][N:23]3[C:45](=[S:29])[NH2:42])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 11412697Thiocarbonyl diimidazoleHCID 67300903HCID 67300903, compound

Product 1

HCID 25096336HCID 25096336, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-[5-(naphthalen-1-yloxy)-pentyloxy]-1,2,3,4-tetrahydro-quinoline (100 mg, 0.28 mmol) and thiocarbonyl diimidazole (64 mg, 0.36 mmol) in dry THF (3 mL) was added triethylamine (30 mg, 0.3 mmol). After stirred at 50° C. for 3 h, the reaction mixture was treated with excess 2.0 M ammonia in methanol (4 mL). The stirring was continued overnight at 50° C. After removal of the solvent, the residue was purified by silica gel chromatography to give 5-[5-(naphthalen-1-yloxy)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carbothioic acid amide, compound 4 (88 mg, 0.21 mmol, 75%) as a white solid. MS (EI): m/z 421 (M+H).

Workup

  1. waitThe stirring was continued overnight at 50° C
  2. customAfter removal of the solvent
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1f347256b3af490bbf28b91e97baa7f5
Source dataset
uspto-grants-2011_07
Patent number
US07985763B2

Reaction notes

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