Ammonium thiocyanate → 1-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)thiourea

HRID 1952181Notes

Reaction equation

HRID 1952181 reaction equation
[NH4+].[N:2]#[C:3][S-:4].[Cl:5][C:6]1[CH:11]=[C:10]([C:12](Cl)=[O:13])[CH:9]=[C:8]([CH3:15])[N:7]=1.[F:16][C:17]1([F:27])[O:21][C:20]2[CH:22]=[CH:23][C:24]([NH2:26])=[CH:25][C:19]=2[O:18]1>CC(=O)C>[Cl:5][C:6]1[CH:11]=[C:10]([C:12]([NH:2][C:3]([NH:26][C:24]2[CH:23]=[CH:22][C:20]3[O:21][C:17]([F:27])([F:16])[O:18][C:19]=3[CH:25]=2)=[S:4])=[O:13])[CH:9]=[C:8]([CH3:15])[N:7]=1

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 27368935-Amino-2,2-difluoro-1,3-benzodioxoleHCID 27821302-Chloro-6-methylpyridine-4-carbonyl chloride

Product 1

HCID 594977661-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)thiourea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Thiocyanic acid, ammonium salt (1:1) (9.35 g; 0.1230 mol) was stirred in 2-propanone (300 ml) at room temperature. 2-Chloro-6-methyl-4-pyridinecarbonylchloride (22.2 g; 0.1170 mol) was then added and the reaction mixture was stirred for 2 hours at room temperature. 2,2-Difluoro-1,3-benzodioxol-5-amine (19.2 g; 0.1110 mol) in some 2-propane was added and the reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was then poured onto ice and the residue was filtered off and dried. Yield: 38.1 g of intermediate D1.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour at room temperature
  2. additionThe reaction mixture was then poured onto ice
  3. filtrationthe residue was filtered off
  4. customdried

Sources & evidence

ORD record
ord-3aa7af4ee2b54407a6ead84d06988b51
Source dataset
uspto-grants-2013_03
Patent number
US08404851B2

Reaction notes

Loading…