2,6-Lutidine → Benzo[d][1,2,3]thiadiazole-7-carbaldehyde

HRID 1769959Notes

Reaction equation

HRID 1769959 reaction equation
[S:1]1[C:5]2[C:6]([C:10](Cl)=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.N1C(C)=CC=CC=1C>C(OCC)(=O)C.O1CCCC1.[Pd]>[S:1]1[C:5]2[C:6]([CH:10]=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 2

HCID 79372,6-LutidineHCID 183776071,2,3-Benzothiadiazole-7-carbonyl chloride

Product 1

HCID 14835681Benzo[d][1,2,3]thiadiazole-7-carbaldehyde

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

99 g of benzo-1,2,3-thiadiazole-7-carboxylic acid chloride are dissolved in 1.21 of ethyl acetate, the mixture is treated at 0°-5° C. with a solution of 58.7 g of 2,6-lutidine in 200 ml of tetrahydrofuran as well as 33 g of palladium/charcoal catalyst (5% Pd), and hydrogenated under low pressure (104Pa) with a further addition of a total of 57 g of palladium/charcoal catalyst and 500 ml of tetrahydrofuran in 5 portions. The catalyst is subsequently removed by filtration and washed with tetrahydrofuran, and the filtrate is evaporated. The residue is purified on silica gel (CH2Cl2) and gives the title compound of m.p. 134°-136° C.

Workup

  1. customThe catalyst is subsequently removed by filtration
  2. washwashed with tetrahydrofuran
  3. customthe filtrate is evaporated
  4. customThe residue is purified on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-04a99c3adeb0431c9bc777e49aae7260
Source dataset
uspto-grants-1995_01
Patent number
US05384321

Reaction notes

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