Methanol → HCID 57572485, compound

HRID 1038289Notes

Reaction equation

HRID 1038289 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([N:17]2[CH2:21][CH2:20][S:19][C:18]2=[S:22])=[O:16])=[CH:13][C:12]([C:23]([N:25]2[CH2:29][CH2:28]SC2=S)=[O:24])=[CH:11][C:10]=1[C:31]([N:33]1[CH2:37][CH2:36][S:35][C:34]1=[S:38])=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39][O:40]CCN.CO>ClCCl>[CH2:1]([O:8][C:9]1[C:14]([C:15]([N:17]2[CH2:21][CH2:20][S:19][C:18]2=[S:22])=[O:16])=[CH:13][C:12]([C:23]([NH:25][CH2:29][CH2:28][O:40][CH3:39])=[O:24])=[CH:11][C:10]=1[C:31]([N:33]1[CH2:37][CH2:36][S:35][C:34]1=[S:38])=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 80182-MethoxyethylamineHCID 57572484HCID 57572484, compound

Product 1

HCID 57572485HCID 57572485, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a slurry of the trithiazolide 17 (31.0 g, 0.05 mol) in dichloromethane (600 mL), a solution of 2-methoxyethylamine (0.38 g, 5 mmol) in dichloromethane (30 mL) was added dropwise over 48 h. The reaction mixture was applied directly onto a gradient flash silica column (1-5% methanol in methylene chloride). The desired product was obtained as yellow, thick oil; yield 2.1 g (73% based on the methoxyethylamine). 25.8 g of unreacted starting trithiazolide was also recovered during the separation.

Sources & evidence

ORD record
ord-4608b5f6f69e46b1b6353b0bc2e3342a
Source dataset
uspto-grants-2013_10
Patent number
US08551453B2

Reaction notes

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