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

HRID 2359910Notes

Reaction equation

HRID 2359910 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-88abeeda0e154a099b749629f2bfe898
Source dataset
uspto-grants-2014_04
Patent number
US08686007B2

Reaction notes

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