Ethyl Bromide → HCID 13557285, compound

HRID 1583491Notes

Reaction equation

HRID 1583491 reaction equation
C[C:2]([N:5]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([Cl:16])[CH:10]=1)[C:6](=[O:8])[O-:7])([CH3:4])C.[CH2:17](Br)C.O1[CH2:24][CH2:23][CH2:22]C1>C(OCC)C>[CH2:2]([N:5]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([Cl:16])[CH:10]=1)[C:6](=[O:8])[O:7][C:23]([CH3:22])([CH3:24])[CH3:17])[CH3:4]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 8028TetrahydrofuranHCID 86740499HCID 86740499, compound

Product 1

HCID 13557285HCID 13557285, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride, 2.0 grams (0.05 mole) was washed repeatedly with heptane, then was stirred in 100 ml of tetrahydrofuran. To this was added 10.0 grams (0.41 mole) of 1,1-dimethylethyl(3-chloro-4-methylphenyl)carbamate (prepared in Example 4, Step A). The reaction was stirred for 5 minutes and 9.0 grams (0.083 mole) of ethyl bromide in 25 ml of tetrahydrofuran was added dropwise. Upon completion of addition the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was taken up in 500 ml of diethyl ether and washed with three 50 ml portions of water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 10.8 grams of 1,1-dimethylethyl N-ethyl-N-(3-chloro-4-methylphenyl)carbamate as an oil.

Workup

  1. washSodium hydride, 2.0 grams (0.05 mole) was washed repeatedly with heptane
  2. stirringThe reaction was stirred for 5 minutes
  3. additionUpon completion of addition the reaction mixture
  4. stirringwas stirred at ambient temperature for 16 hours
  5. washwashed with three 50 ml portions of water
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d22c029f46a4415d9d1aa245dcd2fffd
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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