Dimethylamine → HCID 178484319, compound

HRID 704796Notes

Reaction equation

HRID 704796 reaction equation
[C:1]([N:3]=[C:4](SC)[NH:5][C@@H:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])#[N:2].[CH3:23][NH:24][CH3:25]>>[C:1]([N:3]=[C:4]([N:24]([CH3:25])[CH3:23])[NH:5][C@@H:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[C@H:7]1[OH:20])#[N:2]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 178503932HCID 178503932, compound

Product 1

HCID 178484319HCID 178484319, compound

Procedure

A mixture of (3S,4R)-4-(3-cyano-2-methyl-1-isothioureido)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (16.3 g) and 50% aqueous dimethylamine solution (81.5 ml) was stirred under reflux for 1.5 hours to form white precipitates. These precipitates were collected by filtration, washed with cold water, and recrystallized from ethanol to give (3S,4R)-4-(2-cyano-3,3-dimethylguanidino)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (12.05 g).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customto form white precipitates
  3. filtrationThese precipitates were collected by filtration
  4. washwashed with cold water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-538848ea89e24776a7a142f3dea19547
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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