Acetic Acid → 2-(2-Chloro-5-nitro-benzylamino)-ethanethiol hydrochloride

HRID 1687240Notes

Reaction equation

HRID 1687240 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:12])=[C:8]([CH:11]=1)[CH:9]=O)([O-:3])=[O:2].Cl.[NH2:14][CH2:15][CH2:16][SH:17].C([BH3-])#N.[Na+].C(O)(=O)C>CO>[ClH:12].[Cl:12][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]=1[CH2:9][NH:14][CH2:15][CH2:16][SH:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9082Cysteamine HydrochlorideHCID 729332-Chloro-5-nitrobenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 866338952-(2-Chloro-5-nitro-benzylamino)-ethanethiol hydrochlorideYield 78.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

T a slurry of 5-nitro-2-chloro-benzaldehyde (1.5 g, 0.0078 mol), 2-aminoethanethiol hydrochloride (2.73 g, 0.023 mol), sodium cyanoborohydride (0.49 g, 0.0078 mol) in anhydrous methanol (30 mL) was added acetic acid (5 mL) and stirred 24 hrs. The mixture was evaporated and the residue triturated with isopropanol giving 2-(2-chloro-5-nitro-benzylamino)-ethanethiol hydrochloride (0.87 g, 45%) as a white solid. MP: 228-231° C.; 1H-NMR (DMSO-d6) δ 9.76-82 (br, 2H), 8.75 (s, 1H), 8.28-31 (d, 1H), 7.85-90 (d, 1H), 4.40 (s, 2H), 3.15-25 (m, 2H), 2.80-90 (m, 2H); LC/MS (ESI+): 247 (M+H).

Workup

  1. customThe mixture was evaporated
  2. customthe residue triturated with isopropanol

Sources & evidence

ORD record
ord-799eb21287b04282b9791e5e815c7d70
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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