Hexane → HCID 21253705, compound

HRID 366865Notes

Reaction equation

HRID 366865 reaction equation
[CH2:1]([O:11][C:12]1[C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:15][S:14][C:13]=1[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-])=O)=[CH:30][CH:29]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].O.NN.CCCCCC>C(O)C.[Pt]>[CH2:1]([O:11][C:12]1[C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:15][S:14][C:13]=1[C:28]1[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 8058HexaneHCID 24654Hydrazine hydrate (1:1)HCID 23290212HCID 23290212, compound

Product 1

HCID 21253705HCID 21253705, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(3,4-didecyloxythien-2-yl)-4-nitrobenzene (0.995 g, 1.92 mmol) in 95% ethanol (30 mL) containing platinum on sulfide carbon (30 mg) was added hydrazine hydrate (0.5 mL). The mixture was refluxed for 5 to 10 hours. After cooling, the mixture was filtered and the solvent was evaporated to give a solid. Addition of hexane followed by filtration gave 1-(3,4-didecyloxythien-2-yl)-4-aminobenzene which was subsequently recrystallized from ethanol containing few drops of acetone, 0.855 g. yield=91%, mp=64.5-65.5° C. IR (KBr; cm-1) 3427, 3335, 3116, 2920, 2850, 1624, 1520, 1467, 1372, 1144 and 826. 1H NMR (CDCl3 ; δ in ppm): 0.880 (t, J=7.4 Hz, 6H), 1.381 (m, 28H), 1.700 (m, 4H), 3.947 (m, 4H), 5.992 (s, 1H), 6.674 (d, J=9.5 Hz, 2H) and 7.522 (d, J=9.5 Hz, 2H). 13C NMR (CDCl3 ; δ in ppm): 14.11, 22.69, 25.98, 26.12, 29.17, 29.34, 29.60, 30.09, 30.24, 32.05, 69.75, 72.77, 92.47, 114.96, 123.97, 125.96, 128.06, 141.57, 145.45 and 150.75. MS(EI) m/z (rel int): 487 [(M)+, 40%], 346 [(M+ --C10H21), 8.4%], 207 [(M+ --C20H40), 11%], 178 [(M+ --C21H41O), 8.4%], 150 [(M+ --C22H41O2), 7%] and 136 [(M+ --C23H45NO), 11%]. Anal. Calcd for C30H49NSO2 : C, 73.87; H, 10.13; N, 2.87; S, 6.57. Found: C, 73.99; H, 10.66; N, 2.41; S, 6.32.

Workup

  1. temperatureThe mixture was refluxed for 5 to 10 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customthe solvent was evaporated
  5. customto give a solid
  6. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-ca09085f059840948bdfc888c0f8013c
Source dataset
uspto-grants-2000_10
Patent number
US06130339

Reaction notes

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