Sodium hydride → 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide

HRID 1687558Notes

Reaction equation

HRID 1687558 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].[H-].[Na+].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([Cl:24])=[CH:19][N:18]=1>CN(C)C=O>[Cl:16][C:17]1[N:22]=[C:21]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[C:20]([Cl:24])=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2372592,4,5-TrichloropyrimidineHCID 11328182-amino-N,N-dimethylbenzenesulfonamide

Product 1

HCID 467382872-(2,5-Dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamideYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-N,N-dimethyl-benzenesulfonamide (10.00 g, 49.94 mmol) in N,N-dimethylformamide (200 mL) was treated with sodium hydride 60% dispersion in mineral oil (3.99 g) at 0° C., then 2,4,5-trichloropyrimidine (8.587 mL, 74.90 mmol) was added and the reaction was stirred for 5 minutes at 0° C., then for 3 hours at room temperature. The reaction was quenched with aqueous saturated ammonium chloride, then water. The precipitate was collected by filtration and recrystallized from methanol to give 2-(2,5-dichloro-pyrimidin-4-ylamino)-N,N-dimethyl-benzenesulfonamide as a light grey solid (9.3 g, 52%). LC/MS (ESI+): 346.93 (M+H).

Workup

  1. waitfor 3 hours at room temperature
  2. customThe reaction was quenched with aqueous saturated ammonium chloride
  3. filtrationThe precipitate was collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-17376bf664764a6b851e9f8b7ac1f062
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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