Ammonia → HCID 25096341, compound

HRID 1015431Notes

Reaction equation

HRID 1015431 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH2:16][NH:17]3)=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=[S:25].C([N:38]([CH2:41]C)CC)C.N>C1COCC1.CO>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH2:16][N:17]3[C:41](=[S:25])[NH2:38])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 11412697Thiocarbonyl diimidazoleHCID 67300937HCID 67300937, compound

Product 1

HCID 25096341HCID 25096341, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-1H-indole (100 mg, 0.3 mmol) and thiocarbonyl diimidazole (64 mg, 0.36 mmol) in dry THF (3 mL) was added triethylamine (30 mg, 0.3 mmol). The reaction mixture was stirred at 50° C. for 3 hours and then 2.0 M ammonia in 4 mL methanol (excess) was added. The stirring was continued overnight at 50° C. After removal of the solvent, the residue was purified by silica gel column chromatography to give 4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-indole-1-carbothioic acid amide, compound 8 (101 mg, 0.26 mmol, 85%) as a white solid. MS (EI): m/z 391 (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 column chromatography

Sources & evidence

ORD record
ord-582d5b9b8a63477fb30429da5a937a8c
Source dataset
uspto-grants-2011_07
Patent number
US07985763B2

Reaction notes

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