Dimethylamine → HCID 178484320, compound

HRID 704798Notes

Reaction equation

HRID 704798 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 178503933(3R,4S)-4-(3-cyano-2-methyl-1-isothioureido)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 178484320HCID 178484320, compound

Procedure

A mixture of (3R,4S)-4-(3-cyano-2-methyl-1-isothioureido)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (2.12 g) and 50% aqueous dimethylamine solution (10.6 ml) was stirred under reflux for 1.5 hours to form white precipitates. These precipitates were collected by filtration, washed with water, and recrystallized from ethanol to give (3R, 4S)-4 -(2-cyano-3,3-dimethylguanidino)-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (1.03 g).

Workup

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

Sources & evidence

ORD record
ord-84e468e2d3754787a91da78c10fb199e
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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