Water → 2-Chloro-N-[(2,2-difluoro-benzo[1,3]dioxol-5-ylamino)-methylsulfanyl-methyl]-6-methyl-isonicotinamide

HRID 1952182Notes

Reaction equation

HRID 1952182 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([NH:12][C:13]([NH:15][C:16]2[CH:26]=[CH:25][C:19]3[O:20][C:21]([F:24])([F:23])[O:22][C:18]=3[CH:17]=2)=[S:14])=[O:11])[CH:7]=[C:6]([CH3:27])[N:5]=1.[CH3:28]I.O>C1COCC1>[Cl:3][C:4]1[CH:9]=[C:8]([CH:7]=[C:6]([CH3:27])[N:5]=1)[C:10]([NH:12][CH:13]([NH:15][C:16]1[CH:26]=[CH:25][C:19]2[O:20][C:21]([F:24])([F:23])[O:22][C:18]=2[CH:17]=1)[S:14][CH3:28])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 594977661-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(2,2-difluoro-benzo[1,3]dioxol-5-yl)thiourea

Product 1

HCID 866457122-Chloro-N-[(2,2-difluoro-benzo[1,3]dioxol-5-ylamino)-methylsulfanyl-methyl]-6-methyl-isonicotinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH, 60% (2.2 g; 0.0550 mol) was stirred in THF (170 ml) on an ice bath under N2. Intermediate D1 (19.3 g; 0.500 mol) was then added and stirred for 1 hour at 0° C. CH3I (7.8 g; 0.0550 mol) was then added and the reaction mixture was allowed to warm to room temperature overnight. Water was added and the THF was evaporated in vacuo. The precipitate was filtered off, washed with water and dried. Yield: 22.86 g of intermediate D2.

Workup

  1. temperatureto warm to room temperature overnight
  2. customthe THF was evaporated in vacuo
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b819fa53071144cf83e50504fc5ea6e1
Source dataset
uspto-grants-2013_03
Patent number
US08404851B2

Reaction notes

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