Hydrochloric Acid → N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]methyl]-benzenesulfonamide

HRID 231977Notes

Reaction equation

HRID 231977 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([NH2:18])(=[O:17])=[O:16])=[N:5][N:4]=1.C1([O:25][C:26](=O)[NH:27][C:28]2[N:33]=[C:32]([O:34][CH3:35])[N:31]=[C:30]([CH3:36])[N:29]=2)C=CC=CC=1.C1CCN2C(=NCCC2)CC1.Cl>O1CCOCC1.O>[CH3:35][O:34][C:32]1[N:31]=[C:30]([CH3:36])[N:29]=[C:28]([NH:27][C:26]([NH:18][S:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][C:6]2[S:7][C:3]([S:2][CH3:1])=[N:4][N:5]=2)(=[O:16])=[O:17])=[O:25])[N:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11448329Carbamic acid, (4-methoxy-6-methyl-1,3,5-triazin-2-yl)-, phenyl esterHCID 159257222-[[5-(Methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

Product 1

HCID 15925724N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]methyl]-benzenesulfonamideYield 32.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

By the procedure of Example 4, 0.3 g of the sulfonamide prepared in Example 3 was reacted with 0.29 g of phenyl(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate and 0.15 g of "DBU" in 10 ml of p-dioxane. After stirring two hours at room temperature the solution was diluted with about 75 ml of water and acidified with concentrated hydrochloric acid (red to litmus paper). Following filtration, the residue was washed with water (2×20ml) then with ether (1×20ml) and suction-dried to give 0.15 g of the subject compound; m.p. 140°-146° C. NMR (CDCl3): δ2.6(d,6H,SCH3, OCH3); 4.1 (S, 3H, CH3); 4.9(S, 2H, CH2); 7.4-7.7(m, 4H, Ar+NH); 8.3(d, 1H, Ar).

Workup

  1. filtrationfiltration
  2. washthe residue was washed with water (2×20ml)
  3. dry with materialwith ether (1×20ml) and suction-dried

Sources & evidence

ORD record
ord-acefb080ef4b44a189946b513d6dc3ae
Source dataset
uspto-grants-1989_07
Patent number
US04851030

Reaction notes

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