Imidazole → HCID 86127778, compound

HRID 745534Notes

Reaction equation

HRID 745534 reaction equation
[CH3:1][C:2]([CH3:9])([O:7][CH3:8])[C:3](Cl)=[N:4][OH:5].[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(N(CC)CC)C>O1CCCC1>[CH3:1][C:2]([CH3:9])([O:7][CH3:8])[C:3]([N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)=[N:4][OH:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8471TriethylamineHCID 71356341N-Hydroxy-2-methoxy-2-methylpropanimidoyl chloride

Product 1

HCID 86127778HCID 86127778, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9.9 g (0.066 mol) of 2,2-dimethyl-2-methoxy-1-chloro-1-oximino-ethane is very slowly added dropwise to a mixture of 9.0 g (0.132 mol) of imidazole and 6.7 g (0.066 mol) of triethylamine in 50 ml of absolute tetrahydrofuran at 0° C., with stirring. The mixture is allowed to come to room temperature and is subsequently stirred for 10 hours. The reaction batch is filtered, the filtrate is concentrated and the concentrate is diluted with water. The product which has precipitated is filtered off with suction, washed with petroleum ether and dried. 10.3 g of 2,2-dimethyl-2-methoxy-1-(imidazol-1-yl)-1-oximino-ethane of melting point 155°-160° C. are obtained, that is to say 85% of theory. Intermediate: ##STR65##

Workup

  1. customto come to room temperature
  2. stirringis subsequently stirred for 10 hours
  3. filtrationThe reaction batch is filtered
  4. concentrationthe filtrate is concentrated
  5. additionthe concentrate is diluted with water
  6. customThe product which has precipitated
  7. filtrationis filtered off with suction
  8. washwashed with petroleum ether
  9. customdried

Sources & evidence

ORD record
ord-1caba9085ac24680bb4dcbf19e528a47
Source dataset
uspto-grants-1986_07
Patent number
US04599348

Reaction notes

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