N-[3-(4-Morpholinyl)propyl]thiourea → HCID 14053800, compound

HRID 2352583Notes

Reaction equation

HRID 2352583 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:11])[CH:8]=2)[C:3]1=O.[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][NH:22][C:23]([NH2:25])=[S:24])[CH2:15][CH2:14]1>C(O)C>[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][NH:22][C:23]2[S:24][C:2]3[CH2:10][C:9]4[CH:8]=[C:7]([F:11])[CH:6]=[CH:5][C:4]=4[C:3]=3[N:25]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 2760135N-[3-(4-Morpholinyl)propyl]thioureaHCID 110316412-Bromo-5-fluoro-1-indanone

Product 1

HCID 14053800HCID 14053800, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.5 g of 2-bromo-5-fluoro-1-indanone and 3.1 g of N-(3-morpholinopropyl)thiourea were added to 40 ml of ethanol. The resulting mixture was refluxed for 10 minutes, agitated for 24 hours at room temperature to precipitate crystals which were collected by filtration. The thus collected crystals were washed with ethanol, dried, incorporated with 40 ml of a 5% aqueous solution of NaOH, extracted with ethyl acetate, washed with water, dried, distilled at a reduced pressure and then recrystallized from ethyl acetate-isopropyl ether thereby to obtain 3.9 g of 2-(3-morpholinopropyl)amino-6-fluoro-8H-indeno[1.2-d]thiazole. The thus obtained compound had a melting point of 113° to 115° C. and the following analysis.

Workup

  1. temperatureThe resulting mixture was refluxed for 10 minutes
  2. customto precipitate crystals which
  3. filtrationwere collected by filtration
  4. washThe thus collected crystals were washed with ethanol
  5. customdried
  6. extractionextracted with ethyl acetate
  7. washwashed with water
  8. customdried
  9. distillationdistilled at a reduced pressure
  10. customrecrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-291463488ec04ff183a389a27a58ae26
Source dataset
uspto-grants-1989_10
Patent number
US04877876

Reaction notes

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