Water → N-[5-(1,1-dimethylethyl)-6H-1,3,4-thiadiazin-2-yl]-2,6-dimethoxybenzamide

HRID 1903379Notes

Reaction equation

HRID 1903379 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[N:6][N:7]=1.C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:22]=1[C:23](Cl)=[O:24].O>O1CCOCC1>[CH3:9][C:8]([C:5]1[CH2:4][S:3][C:2]([NH:1][C:23](=[O:24])[C:22]2[C:26]([O:30][CH3:31])=[CH:27][CH:28]=[CH:29][C:21]=2[O:20][CH3:19])=[N:7][N:6]=1)([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 748102,6-Dimethoxybenzoyl chlorideHCID 132682032-amino-5-(1,1-dimethylethyl)-6H-1,3,4-thiadiazine

Product 1

HCID 13268205N-[5-(1,1-dimethylethyl)-6H-1,3,4-thiadiazin-2-yl]-2,6-dimethoxybenzamideYield 12.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.71 g of 2-amino-5-(1,1-dimethylethyl)-6H-1,3,4-thiadiazine and 1.01 g triethylamine in 18 ml dioxane was added 2.11 g of 2,6-dimethoxybenzoyl chloride. The reaction mixture was stirred at room temperature for 3 hours and poured into 100 ml water. The solid was collected and recrystallized from ethanol. The second crop of material provided 0.43 g of N-[5-(1,1-dimethylethyl)-6H-1,3,4-thiadiazin-2-yl]-2,6-dimethoxybenzamide. mp=175°-177° C.

Workup

  1. customThe solid was collected
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-09556581192342388446d0af43de30dd
Source dataset
uspto-grants-1984_03
Patent number
US04436549

Reaction notes

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