Trifluoroacetic acid → 3-(4-(Methylsulfonyl)phenyl)-1,2,4-thiadiazol-5-amine

HRID 2190309Notes

Reaction equation

HRID 2190309 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([NH:16]C(=O)OC(C)(C)C)[S:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:15]=[C:14]([NH2:16])[S:13][N:12]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 68743050Tert-butyl 3-(4-(methylsulfonyl)phenyl)-1,2,4-thiadiazol-5-ylcarbamate

Product 1

HCID 337802353-(4-(Methylsulfonyl)phenyl)-1,2,4-thiadiazol-5-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(methylsulfonyl)phenyl)-1,2,4-thiadiazol-5-ylcarbamate (1.57 g, 4.42 mmol) in DCM (20 mL) was added anisol (0.50 mL) and TFA (10 mL). The reaction mixture was stirred at room temperature for 6 h and concentrated. The solid was suspended in saturated NaHCO3 (˜200 mL) and stirred for 30 min. The solid was collected by filtration, washed with water (˜500 mL) followed by hexanes (˜50 mL), and dried under high vacuum to give 3-(4-(methylsulfonyl)phenyl)-1,2,4-thiadiazol-5-amine.

Workup

  1. concentrationconcentrated
  2. stirringstirred for 30 min
  3. filtrationThe solid was collected by filtration
  4. washwashed with water (˜500 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-b3d19bf62c444c7f9aad97744038cd74
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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