Ethanol → HCID 21182578, compound

HRID 2280221Notes

Reaction equation

HRID 2280221 reaction equation
[C:1]([S:20][CH2:21][CH2:22][CH2:23][CH2:24]CCC1C=CC=C2C(NC(=O)C=12)=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:39]N.[CH2:41](O)[CH3:42]>>[C:1]([S:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:41][CH2:42][NH2:39])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 66603941HCID 66603941, compound

Product 1

HCID 21182578HCID 21182578, compoundYield 95%

Procedure

6-(S-Trityl-)mercaptohexylphthalimide (14.27 g, 28.2 mmol) was suspended in ethanol (250 mL). Hydrazine hydrate (3.45 mL, 70.5 mmol) was added, and the mixture was heated to reflux for 2 h. The mixture was filtered and the filtrate was concentrated in vacuo. Chloroform (180 mL) was added to the residual oil and the resulting suspension was stirred at room temperature for 1.5 h. The mixture was filtered, and the filtrate was extracted with water (60 mL) and brine (60 mL), dried over MgSO4 and concentrated to yield crude 6-(tritylmercapto)-hexylamine (10.10 g, 26.87 mmol, 95%). MS: m/z 376.22=[M+H]+, (calculated=376.20).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionChloroform (180 mL) was added to the residual oil
  6. filtrationThe mixture was filtered
  7. extractionthe filtrate was extracted with water (60 mL) and brine (60 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d6bd5758d8af4c59856eb822adfe2eb0
Source dataset
uspto-grants-2015_09
Patent number
US09138462B2

Reaction notes

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