Triethylamine → 1,1,3-Trimethyl-3-[5-(3-methylisoxazol-5-yl-methylthio)-1,3,4-thiadiazol-2-yl]urea

HRID 482800Notes

Reaction equation

HRID 482800 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7]Cl)[O:4][N:3]=1.[CH3:9][N:10]([CH3:21])[C:11]([N:13]([CH3:20])[C:14]1[S:15][C:16]([SH:19])=[N:17][N:18]=1)=[O:12].C(N(CC)CC)C>O1CCCC1>[CH3:9][N:10]([CH3:21])[C:11]([N:13]([CH3:20])[C:14]1[S:15][C:16]([S:19][CH2:7][C:5]2[O:4][N:3]=[C:2]([CH3:1])[CH:6]=2)=[N:17][N:18]=1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 71314965-(Chloromethyl)-3-methyl-1,2-oxazoleHCID 178484698HCID 178484698, compound

Product 1

HCID 136034851,1,3-Trimethyl-3-[5-(3-methylisoxazol-5-yl-methylthio)-1,3,4-thiadiazol-2-yl]ureaYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 ml round bottom flask were mixed 3-methyl-5-chloromethylisoxazole (1.5 g, 11 mmol), tetrahydrofuran (50 ml), 1,1,3-trimethyl-3-(5-mercapto-1,3,4-thiadiazol-2-yl) urea (2.5 g, 11 mmol) and triethylamine (5.1 g, 50 mmol). This was stirred at room temperature overnight. The reaction mixture was filtered and the solvent was stripped from the filtrate on a rotary evaporator. The residue was dissolved in dichloromethane and this was washed with water (2×60 ml) and the organic solution was dried over MgSO4. This was treated with decolorizing carbon, was filtered and the solvent was removed to give a pale tan oil which was dried in vacuo, 2.9 g, 84.1% yield. NMR: (CDCl3) 6.2 (S, 1H), 4.5 (S, 2H), 3.55 (S, 3H), 2.95 (S, 6H), 2.25 (S, 3H). IR (neat) 3120, 2960, 2930, 1660, 1600, 1480, 1440, 1410, 1370 1305, 1265, 1125, 1080, 1060 cm-1. Calcd: C, 42.16; H, 4.82; N, 22.35. Found: C, 42.06; H, 4.90; N, 22.10.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was stripped from the filtrate on a rotary evaporator
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washthis was washed with water (2×60 ml)
  5. dry with materialthe organic solution was dried over MgSO4
  6. additionThis was treated with decolorizing carbon
  7. filtrationwas filtered
  8. customthe solvent was removed
  9. customto give a pale tan oil which
  10. customwas dried in vacuo, 2.9 g, 84.1% yield

Sources & evidence

ORD record
ord-d5e4ca946eed485db3ba0f7bd9248970
Source dataset
uspto-grants-1986_03
Patent number
US04576629

Reaction notes

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