(1,1-Dimethylethyl)urea → HCID 20064756, compound

HRID 359296Notes

Reaction equation

HRID 359296 reaction equation
Cl[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])[C:3](=O)[C:4]([O:6][CH3:7])=[O:5].[C:16]([NH:20][C:21]([NH2:23])=[O:22])([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[CH3:17][C:16]([NH:20][C:21]1[O:22][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[N:23]=1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 14233(1,1-Dimethylethyl)ureaHCID 20064768HCID 20064768, compound

Product 1

HCID 20064756HCID 20064756, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the procedure of Example 50, 12.35 g (50 mmol) of methyl 3-chloro-3-(o-chlorophenyl)pyruvate was reacted with 5.8 g (50 mmol) of tert-butyl urea at 105°-115° C. for 8 hours. The reaction mixture was cooled to ambient temperature and then diluted with methylene chloride, washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to yield a yellow oil. This oil was purified by flash chromatography techniques on silic gel using 10% ethyl acetate in hexane as eluent. There was obtained 5.77 g of an orange viscous oil product identified in Table I.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto yield a yellow oil
  5. customThis oil was purified by flash chromatography techniques on silic gel

Sources & evidence

ORD record
ord-95045da47a514adeb2c26dc6c88747c5
Source dataset
uspto-grants-1991_03
Patent number
US05000775

Reaction notes

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