Dimethylacetamide → HCID 86660796, compound

HRID 1913842Notes

Reaction equation

HRID 1913842 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[S:9]([OH:12])(=[O:11])=[O:10].[Na].[CH3:14][C:15](N(C)C)=O>[Cu].O>[Br:8][C:5]1[CH:4]=[C:3]([S:9]([OH:12])(=[O:11])=[O:10])[C:2]([C:2]2[C:3]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:4][C:5]([Br:8])=[CH:14][CH:15]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 31374DimethylacetamideHCID 5251666HCID 5251666, compoundHCID 5360545Sodium2×

Product 1

HCID 86660796HCID 86660796, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A modification of the published procedures of Courtot and Lin in Bull. Soc. Chim. Fr. 1931, 49, 1047 was used. Inside a glove box, a 500 mL round-bottom flask equipped with a reflux condenser, stirring bar, and gas inlet was charged with 2,5-dibromobenzenesulfonic acid, sodium salt (73 g, 0.216 moles), activated copper bronze (27 g, 0.43 moles), and DMAc (200 mL). The mixture was heated to 120° C. overnight under nitrogen. The mixture was poured into water (1 L) and the solid removed by vacuum filtration. The filtrate was evaporated and the residue dried at 100° C. under vacuum. The solids were recrystallized from acetonitrile/water (10:1) after treating with decolorizing carbon and dried under vacuum at 60-150° C. to give 48.13 g (86% yield) of 4,4′-dibromobiphenyl-2,2′-disulfonic acid, sodium salt. 1H NMR (DMSO-d6): 7.19 (d, 8.3 Hz, 2H), 7.42 (dd, 8.3 and 2.1 Hz, 2H), 7.96 (d, 2.1 Hz, 2H).

Workup

  1. customInside a glove box, a 500 mL round-bottom flask equipped with a reflux condenser
  2. customthe solid removed by vacuum filtration
  3. customThe filtrate was evaporated
  4. customthe residue dried at 100° C. under vacuum
  5. customThe solids were recrystallized from acetonitrile/water (10:1)
  6. additionafter treating with decolorizing carbon
  7. customdried under vacuum at 60-150° C.

Sources & evidence

ORD record
ord-eec6b1c84e5e4d70a9779bbadecbd8cb
Source dataset
uspto-grants-2013_12
Patent number
US08609804B2

Reaction notes

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