Dichloromethane → 3-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-thiadiazol-5-amine

HRID 922701Notes

Reaction equation

HRID 922701 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][NH2:10])=[CH:4][CH:3]=1.C[CH2:14][N:15]([CH:19](C)C)C(C)C.ClN1C=C(Cl)[S:25][NH:24]1.C(Cl)[Cl:30]>>[Cl:30][C:19]1[N:15]=[C:14]([NH:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)([CH3:12])[CH3:11])[S:25][N:24]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amineHCID 866736213,5-Dichlorothiadiazole

Product 1

HCID 709750603-Chloro-N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-thiadiazol-5-amineYield 94%

Procedure

To a 0° C. solution of 2-(4-fluorophenyl)-2-methylpropan-1-amine (16.8 g, 101 mmol, 1.0 equiv) and DIPEA (35 mL, 200 mmol, 2.0 equiv) in dry DCM (350 mL) was slowly added 3,5-dichlorothiadiazole (15.5 g, 101 mmol, 1.0 equiv). The reaction was allowed to stir at room temperature until starting material was consumed as judged by HPLC/MS. The reaction was diluted with water and EtOAc. The layers were separated, and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide the title compound as a yellow-orange oil (27 g, 94%). m/z=284.1 [M+H]+.

Workup

  1. customTo a 0° C.
  2. customwas consumed
  3. additionThe reaction was diluted with water and EtOAc
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f526f4c3d714988a1ea7d462dc3ceff
Source dataset
uspto-grants-2016_03
Patent number
US09278962B2

Reaction notes

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