Sodium Hydroxide → HCID 69148958, compound

HRID 1297334Notes

Reaction equation

HRID 1297334 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]2[N:32]=[C:31]3[S:33][C:34]([C:36]([OH:38])=O)=[CH:35][N:30]3[C:29]=2[CH:39]=1.[O:40]1[CH2:44][CH2:43][O:42][CH:41]1[CH2:45][NH:46][CH3:47].[OH-].[Na+]>CN(C=O)C>[O:40]1[CH2:44][CH2:43][O:42][CH:41]1[CH2:45][N:46]([CH3:47])[C:36]([C:34]1[S:33][C:31]2=[N:32][C:28]3[CH:27]=[CH:26][C:25]([CH2:24][OH:23])=[CH:39][C:29]=3[N:30]2[CH:35]=1)=[O:38]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 5417541,3-Dioxolane-2-methanamine, N-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12109531HCID 12109531, compound

Product 1

HCID 69148958HCID 69148958, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (10.1 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (28.8 g) were added to a DMF (500 ml) suspension of 6-hydroxymethylthiazolo[3,2-a]benzimidazole-2-carboxylic acid (12.4 g), and the reaction mixture was stirred at room temperature for 1.5 hours. N-(1,3-Dioxolan-2-ylmethyl)-N-methylamine (17.1 ml) was added to the reaction mixture, and the resulting reaction mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into 0.5 M sodium hydroxide aqueous solution (2 l). The insoluble matter was collected by filtration, washed with water and then with a mixed solvent of hexane and diethyl ether (mixing ratio; 3:1) and then dried by heating under a reduced pressure to obtain the title compound (8.62 g).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at the same temperature for 1 hour
  3. customAfter completion of the reaction
  4. filtrationThe insoluble matter was collected by filtration
  5. washwashed with water
  6. dry with materialwith a mixed solvent of hexane and diethyl ether (mixing ratio; 3:1) and then dried
  7. temperatureby heating under a reduced pressure

Sources & evidence

ORD record
ord-714346f70d964eb8b952102dc9ed2614
Source dataset
uspto-grants-2007_07
Patent number
US07250429B2

Reaction notes

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