Triethylamine → HCID 54333064, compound

HRID 2352485Notes

Reaction equation

HRID 2352485 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]=[CH:5]2.C(N(CC)CC)C.[C:27](Cl)(Cl)=[S:28]>CN(C)C(=O)C.C(#N)C>[N:1]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[CH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:6]=[CH:5]2)=[C:27]=[S:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 54111985HCID 54111985, compound

Product 1

HCID 54333064HCID 54333064, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 24.6 g of 6-amino-2-styrylquinoline and 22.3 g of triethylamine in 100 ml of N,N-dimethylacetamide was added dropwise to 12.5 g of thiophosgene in 25 ml of acetonitrile with the temperature kept at or below -10° C. using a dry ice bath. After reacting for 5 hours at room temperature, the solid was filtered off and 500 ml of chloroform were added to the filtrate. The deposited solid was filtered off and the filtrate was separated and purified by silica gel column chromatography (the developing solution: chloroform). The obtained solid was recrystallized by using ethyl acetate to yield 19.3 g (67% of the theoretical yield) of 6-isothiocyanato-2-styrylquinoline.

Workup

  1. custombelow -10° C.
  2. filtrationthe solid was filtered off
  3. addition500 ml of chloroform were added to the filtrate
  4. filtrationThe deposited solid was filtered off
  5. customthe filtrate was separated
  6. custompurified by silica gel column chromatography (the developing solution
  7. customThe obtained solid was recrystallized
  8. customto yield 19.3 g (67% of the

Sources & evidence

ORD record
ord-e991c754ac1c4b9e943b7878e02db93b
Source dataset
uspto-grants-1989_10
Patent number
US04877723

Reaction notes

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