Dimethyl N-cyanodithioiminocarbonate → HCID 178431170, compound

HRID 344773Notes

Reaction equation

HRID 344773 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C@@H:5]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:18])([CH3:17])[C@H:6]1[OH:19].CS[C:22](SC)=[N:23][C:24]#[N:25]>C1(C)C=CC=CC=1>[C:15]([C:12]1[CH:13]=[CH:14][C:9]2[O:8][C:7]([CH3:17])([CH3:18])[C@@H:6]([OH:19])[C@H:5]([N:4]3[CH2:3][CH2:2][NH:1][C:22]3=[N:23][C:24]#[N:25])[C:10]=2[CH:11]=1)#[N:16]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 15680853trans-4-(2-Aminoethylamino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol

Product 1

HCID 178431170HCID 178431170, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of trans-4-(2-aminoethylamino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol (D3) (0.39g) and dimethyl N-cyanodithioiminocarbonate (0.158g) was heated under reflux in toluene (30 ml) for 71 h. The solvent was evaporated in vacuo, and the residue column chromatographed (Kieselgel 60, gradient elution: 2-7% methanol-chloroform) giving the title compound as a white solid (0.33g). Recrystallisation from ethyl acetate-ether gave a sample of m.p. 257°-260° C.

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated in vacuo
  3. customthe residue column chromatographed
  4. wash(Kieselgel 60, gradient elution: 2-7% methanol-chloroform)

Sources & evidence

ORD record
ord-57b3616783734e4a8fa0c1ecb97e6c2e
Source dataset
uspto-grants-1991_10
Patent number
US05053427

Reaction notes

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