Methanol → HCID 57572488, compound

HRID 1038281Notes

Reaction equation

HRID 1038281 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([N:11]2[CH2:15][CH2:14][S:13][C:12]2=[S:16])=[O:10])=[CH:7][C:6]([C:17]([N:19]2CCS[C:20]2=S)=[O:18])=[CH:5][C:4]=1[C:25]([N:27]1[CH2:31][CH2:30][S:29][C:28]1=[S:32])=[O:26].CN.C(O)(C)C.CO>ClCCl>[CH3:1][O:2][C:3]1[C:4]([C:25]([N:27]2[CH2:31][CH2:30][S:29][C:28]2=[S:32])=[O:26])=[CH:5][C:6]([C:17]([NH:19][CH3:20])=[O:18])=[CH:7][C:8]=1[C:9]([N:11]1[CH2:15][CH2:14][S:13][C:12]1=[S:16])=[O:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 3776IsopropanolHCID 6329MethylamineHCID 57572464HCID 57572464, compound

Product 1

HCID 57572488HCID 57572488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of the trithiazolide 5 (27.1 g, 0.05 mol) in dichloromethane (600 mL), a mixture of 2 mL methylamine solution (40% wt in water, d=0.902) and isopropanol (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 a thick, yellow oil, yield 7.5 g (71% based on the methylamine). 12.8 g of unreacted starting trithiazolide was recovered during the separation.

Workup

  1. additionwas added dropwise over 48 h

Sources & evidence

ORD record
ord-75d9f7e0fef5496489389c918401f4d7
Source dataset
uspto-grants-2013_10
Patent number
US08551453B2

Reaction notes

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