Propyl mercaptan → HCID 57467374, compound

HRID 510564Notes

Reaction equation

HRID 510564 reaction equation
[H-].[Na+].[CH2:3]([SH:6])[CH2:4][CH3:5].C(N(CC)CC)C.Br[CH2:15][CH2:16][C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][CH:23]([NH:35][C:36](=[O:40])[O:37][CH2:38][CH3:39])[CH:24]2[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)=[CH:19][CH:18]=1>CN(C=O)C>[CH2:38]([O:37][C:36](=[O:40])[NH:35][CH:23]1[CH2:22][CH2:21][C:20]2[C:25](=[CH:26][C:17]([CH2:16][CH2:15][S:6][CH2:3][CH2:4][CH3:5])=[CH:18][CH:19]=2)[CH:24]1[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)[CH3:39]

Participants

6

Reactant 4

HCID 7848Propyl mercaptanHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 57467372HCID 57467372, compound

Product 1

HCID 57467374HCID 57467374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (4.73 mg, 0.177 mmol) in 3 ml dry DMF under N2 was added 1-propanthiol (0.012 ml, 0.133 mmol, dissolved in 1 ml dry DMF). The reaction was stirred at room temperature for 2 h, followed by addition of triethylamine (0.019 ml, 0.133 mmol) and ethyl 7-(2-bromoethyl)-1-(3-chlorobenzyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (40 mg, 0.089 mmol, dissolved in 2 ml dry DMF). The mixture was stirred at room temperature over night, the solvent evaporated, the residue re-dissolved in ethyl acetate, washed with water, citric acid, NaHCO3 and brine and filtered. The solvent was evaporated to obtain 31 mg of an off white solid which was used without further purification.

Workup

  1. stirringThe mixture was stirred at room temperature over night
  2. customthe solvent evaporated
  3. dissolutionthe residue re-dissolved in ethyl acetate
  4. washwashed with water, citric acid, NaHCO3 and brine
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. customto obtain 31 mg of an off white solid which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-80f9c33011614de59f78140ba4c0dc8a
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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