Triethylamine → HCID 71209099, compound

HRID 59883Notes

Reaction equation

HRID 59883 reaction equation
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)[C:3]([NH2:5])=[S:4].C(N(CC)CC)C.[C:35](Cl)(=[O:39])[C:36](Cl)=[O:37]>CCOC(C)=O>[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:25])[F:26])=[CH:19][CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)[C:3]1[S:4][C:35](=[O:39])[C:36](=[O:37])[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86675817HCID 86675817, compound

Product 1

HCID 71209099HCID 71209099, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a flask containing EtOAc (30 mL) was added 1-methyl-1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)thiourea (0.600 g, 1.52 mmol) and triethylamine (510 μl, 3.66 mmol). A solution of oxalyl chloride (467 mL, 5.34 mmol) in EtOAc (24 mL) was added and the solution was stirred at ambient temperature for 15 min Evaporation of solvent in vacuo left a white-yellow solid which was dissolved in 50 mL of dichloromethane and washed with water (3×25 mL). The organic layer was dried (MgSO4) and concentrated to furnish 2-(methyl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)amino)thiazole-4,5-dione as an orange solid (632 mg, 92%): mp 114-118° C.; 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.36 (d, J=8.7 Hz, 2H), 7.82 (d, J=9.1 Hz, 2H), 7.50-7.34 (m, 4H), 3.82 (s, 3H); ESIMS m/z 448 ([M+H]+).

Workup

  1. customEvaporation of solvent in vacuo
  2. waitleft a white-yellow solid which
  3. dissolutionwas dissolved in 50 mL of dichloromethane
  4. washwashed with water (3×25 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82bd43dbf0fd47b9b8c1493c41544263
Source dataset
uspto-grants-2016_09
Patent number
US09440964B2

Reaction notes

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