Hydrochloric Acid → (S)-1-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)ethanamine

HRID 57407Notes

Reaction equation

HRID 57407 reaction equation
Cl.C(OC(=O)[NH:8][C@H:9]([C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[N:14][N:15]=1)[CH3:10])(C)(C)C>O1CCOCC1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[S:12][C:11]([C@@H:9]([NH2:8])[CH3:10])=[N:15][N:14]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90451724HCID 90451724, compound

Product 1

HCID 90416777(S)-1-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)ethanamineYield 113.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of hydrogen chloride (4.0 M in 1,4-dioxane, 4 mL, 16 mmol, 9 equiv) was added to a solution of (S)-tert-butyl(1-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)ethyl)carbamate (600 mg, 1.77 mmol) in 1,4-dioxane (5 mL) at room temperature. The solution was stirred for 3 hours, by which time a white precipitate had formed. The reaction was concentrated in vacuo to give the hydrochloride salt of (S)-1-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)ethanamine (480 mg, white solid) in 97% yield. The material was used without purification. 1H NMR (400 MHz, CD3OD) δ 8.00 (d, J=8.7 Hz, 2H), 7.58 (d, J=8.7 Hz, 2H), 5.10 (q, J=6.9 Hz, 1H), 1.82 (d, J=6.9 Hz, 3H). MS m/z 240.0 (M+H)+; Rt-0.54 min.

Workup

  1. customhad formed
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-3679daf963684fedadcd958540a7eb42
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

Loading…