1,2-Dimethoxyethane → HCID 178512278, compound

HRID 1378428Notes

Reaction equation

HRID 1378428 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][F:11])=[N:6][CH:7]=1.[CH:12]1[CH:17]=[CH:16][C:15]([O:18][C:19](OC2C=CC=CC=2)=[N:20][C:21]#[N:22])=[CH:14][CH:13]=1.COCCOC>CCOCC>[F:11][CH2:10][CH2:9][NH:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:19](=[N:20][C:21]#[N:22])[O:18][C:15]2[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 688090Diphenyl N-CyanocarbonimidateHCID 22911640HCID 22911640, compound

Product 1

HCID 178512278HCID 178512278, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of the product from Step 2 (0.0112 mol), diphenylcyanocarbonimidate (2.67 g, 0.0112 mol) and ethylene glycol dimethyl ether (25 ml) was kept under nitrogen for 18 hours at 24° C. The mixture was diluted with Et2O (25 ml) and the solid was collected by filtration to give 1.04 g, mp 157°-158° C. of the titled product. The filtrate was purified by silica gel chromatography with 2.5% MeOH--CHcl3 to give 0.39 g of additional product: MS m/z (relative intensity) 299 (M+, 100), 278 (23.5), 266 (24.4), 206 (37.7), 184 (42.6), 172 (68.3), 94 (95.4).

Workup

  1. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-e2ede3df3ffb4e92a71bd4b7328d1ec2
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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