Diisopropylethylamine → 3-(Chloromethyl)-N-[(2,4-dimethoxyphenyl)methyl]-1,2,4-thiadiazol-5-amine

HRID 1020271Notes

Reaction equation

HRID 1020271 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([CH2:7][Cl:8])[N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].CCN(C(C)C)C(C)C>C1COCC1>[Cl:8][CH2:7][C:4]1[N:3]=[C:2]([NH:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[O:10][CH3:9])[S:6][N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazoleHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 580550883-(Chloromethyl)-N-[(2,4-dimethoxyphenyl)methyl]-1,2,4-thiadiazol-5-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-3-chloromethyl-[1,2,4]thiadiazole (10 mmol) is added to a solution of 2,4-dimethoxybenzylamine (10 mmol) in THF at room temperature followed by addition of DIEA (10 mmol). The mixture is stirred overnight. The white precipitate is filtered and washed with THF. The filtrate is concentrated to oil and dried under high vacuum.

Workup

  1. filtrationThe white precipitate is filtered
  2. washwashed with THF
  3. concentrationThe filtrate is concentrated to oil
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-933dc3d9cef64b1abaa1534c83b7617a
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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