Benzylamine → HCID 15574323, compound

HRID 1168423Notes

Reaction equation

HRID 1168423 reaction equation
Cl[C:2]1[C:3]([N+]([O-])=O)=[N:4][S:5][N:6]=1.C(N(CC)CC)C.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C[N:26]1[C:30](=O)[CH2:29][CH2:28][CH2:27]1>C(O)C.[Pd]>[NH2:26][C:27]1[C:3]2[C:2](=[N:6][S:5][N:4]=2)[CH:30]=[CH:29][C:28]=1[NH:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 22992371HCID 22992371, compound

Product 1

HCID 15574323HCID 15574323, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-chloro-4-nitro-2,1,3-thiadiazole (1.0 g, 4.64 mmol) in anhydrous NMP (5 ml) was added triethylamine (0.65 ml, 4.64 mmol) and benzylamine (0.51 ml, 4.64 mmol). The mixture was heated to 80° C. for 1 hour. The cooled mixture was poured into ice-water (50 ml) and the product was filtered off, washed with water and dried. Yield: 1 g (75%). This product (0.5 g, 1.75 mmol) was suspended in ethanol (20 ml) and hydrogenated at ambient pressure using palladium (5% on activated carbon) as the catalyst. Yield: quantitative.

Workup

  1. filtrationthe product was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-7c29bc13772c42acb2c65808376d7e4b
Source dataset
uspto-grants-2003_09
Patent number
US06624186B2

Reaction notes

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