Potassium Carbonate → HCID 11046378, compound

HRID 1824588Notes

Reaction equation

HRID 1824588 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](Cl)=[CH:4][C:3]=1[NH2:12].[SH:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[C:16]([N:18]([CH3:20])[CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:12][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[C:5]([S:13][C:14]2[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=2[C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 231082,5-Dichloro-4-nitroanilineHCID 88718o-Mercapto-N,N-dimethylbenzamide

Product 1

HCID 11046378HCID 11046378, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.5-dichloro-4-nitro-phenylamine (17) (3.0 g, 14.5 mmol) and 2-mercapto-N,N-dimethyl-benzamide (3.0 g, 16.6 mmol) in DMF (50 mL) was heated to reflux with potassium carbonate (10 g) for 24 h. The mixture was poured into ice water and the precipitate was collected by a filtration. A dark colored solid was recrystalized from petroleum ether/methylene chloride yielded 3.8 g of (18) as a pale yellow powder (75%): IR (cm−1, KBr) 3461, 3376, 3153, 3154, 1627, 1575, 1492, 1135; 1H NMR (200 MHz CDCl3) δ 8.23 (s, 1H), 7.3–7.6 (m, 4H), 6.16 (s, 1H), 4.8 (br s, 2H), 3.37 (s, 3H), 2.86 (s, 3H). Anal. (C15H14ClN3O3S) C, H, N.

Workup

  1. filtrationthe precipitate was collected by a filtration
  2. customA dark colored solid was recrystalized from petroleum ether/methylene chloride

Sources & evidence

ORD record
ord-907cf24006a04f4cb20febfb67c5dd80
Source dataset
uspto-grants-2006_05
Patent number
US07041851B2

Reaction notes

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