Sodium hydride → HCID 178485056, compound

HRID 426493Notes

Reaction equation

HRID 426493 reaction equation
[C:1]([N:3]=[C:4]([NH:9][CH3:10])[NH:5][CH2:6][CH2:7][SH:8])#[N:2].[H-].[Na+].Cl[CH2:14][C:15]1[O:19][C:18]([CH2:20][N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])=[CH:17][CH:16]=1>CN(C)C=O>[C:1]([N:3]=[C:4]([NH:9][CH3:10])[NH:5][CH2:6][CH2:7][S:8][CH2:14][C:15]1[O:19][C:18]([CH2:20][N:21]2[C:22](=[O:31])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]2=[O:30])=[CH:17][CH:16]=1)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 234521252-[[5-(Chloromethyl)-2-furanyl]methyl]-1H-isoindole-1,3(2H)-dioneHCID 178485054HCID 178485054, compound

Product 1

HCID 178485056HCID 178485056, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of N"-cyano-N-(2-mercaptoethyl)-N'-methylguanidine (1.0 g) and sodium hydride (0.152 g) in dry dimethylformamide (4 ml) at room temperature was added slowly a solution of 2-(5-chloromethyl-2-furanylmethyl)-1H-isoindole-1,3(2H)-dione (1.74 g) in dry dimethylformamide (8 ml). After stirring for 2 hr in the solution was evaporated to dryness and the oily residue suspended in an ethyl acetate (25 ml)-water (20 ml) mixture. The solid residue was filtered and crystallised from methanol to give the title compound (1.4 g) m.p. 179°-182°.

Workup

  1. customwas evaporated to dryness
  2. filtrationThe solid residue was filtered
  3. customcrystallised from methanol

Sources & evidence

ORD record
ord-8629165972b748788cfb2b71bdf63c3c
Source dataset
uspto-grants-1979_10
Patent number
US04169855

Reaction notes

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