Ethanol → HCID 21182578, compound

HRID 1776126Notes

Reaction equation

HRID 1776126 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%).

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-2be48bc7b0fc45cdb5fd8d9ff0234919
Source dataset
uspto-grants-2016_02
Patent number
US09265723B2

Reaction notes

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