Thiophosgene → HCID 86683465, compound

HRID 515790Notes

Reaction equation

HRID 515790 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[N:4][CH:3]=1.[C:14](Cl)(Cl)=[S:15]>CC(N(C)C)=O.CCOC(C)=O.O>[N:1]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]#[N:13])=[N:4][CH:3]=1)=[C:14]=[S:15]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 218752724-Aminoisoquinoline-1-carbonitrile

Product 1

HCID 86683465HCID 86683465, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

A mixture of 4-aminoisoquinoline-1-carbonitrile (500 mg, 2.95 mmol) and thiophosgene (0.34 mL, 4.44 mmol) in DMA (5 mL) was stirred at room temperature overnight. The mixture was diluted with EtOAc/water. The two layers were separated and the aqueous layer was extracted with EtOAc (3×). The organics were combined, washed with a saturated solution of sodium bicarbonate (2×), dried over sodium sulfate, and evaporated to dryness to afford 553 mg of 4-isothiocyanatoisoquinoline-1-carbonitrile as an orange oil. 1H NMR (300 MHz, DMSO-d6) δ 8.88 (s, 1H), 8.32 (d, 1H), 8.23 (d, 1H), 8.12 (td, 1H), 8.05 (td, 1H).

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (3×)
  3. washwashed with a saturated solution of sodium bicarbonate (2×)
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-348cf7b346d04560804b365e3053f666
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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