Cyanogen Bromide → HCID 58426082, compound

HRID 1877328Notes

Reaction equation

HRID 1877328 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[NH:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.[N:16]#[C:17]Br>C(#N)C>[CH:7]1([N:6]=[C:2]2[N:3]([C:17]#[N:16])[CH2:4][CH2:5][S:1]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 25191688N-(2,3-Dihydro-1H-inden-1-yl)-4,5-dihydro-1,3-thiazol-2-amine

Product 1

HCID 58426082HCID 58426082, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 0.70 g (3.2 mmol) (4,5-Dihydro-thiazol-2-yl)-indan-1-yl-amine, 0.52 g (4.8 mmol) cyanogen bromide and 1.56 g (4.8 mmol) CsCO3 in 10 ml acetonitrile—was stirred at 20° C. for 16 hours. The suspension was filtered and the solvent evaporated. The crude product was purified by flash chromatography using EtOAc/n-hexane (1:5) as eluent to yield 0.50 g of 2-(Indan-1-ylimino)-thiazolidine-3-carbonitrile (white crystals, m.p. 90-91° C.). 1H-NMR (400 MHz, CDCl3): 2.0-2.15 (1H, m); 2.40-2.50 (1H, m); 2.85-2.95 (1H, m); 3.0-3.10 (1H, m); 3.35-3.45 (2H, m), 3.90-4.0 (2H, m), 4.65 (1H, t), 7.10-7.30 (4H, m).

Workup

  1. filtrationThe suspension was filtered
  2. customthe solvent evaporated
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5dab425e776b444c819b2833702f37d6
Source dataset
uspto-grants-2012_11
Patent number
US08309739B2

Reaction notes

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