Triethylamine → HCID 54384183, compound

HRID 437718Notes

Reaction equation

HRID 437718 reaction equation
[C:1]([C:3]1[C:4]([CH:14]([CH3:16])[CH3:15])=[N:5][S:6][C:7]=1[NH:8][C:9](=O)[N:10]([CH3:12])[CH3:11])#[N:2].P(Br)(Br)([Br:19])=O.C(N(CC)CC)C>C1C=CC=CC=1>[C:1]([C:3]1[C:4]([CH:14]([CH3:16])[CH3:15])=[N:5][S:6][C:7]=1[N:8]=[C:9]([Br:19])[N:10]([CH3:12])[CH3:11])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24613Phosphorus oxybromideHCID 21426762HCID 21426762, compound

Product 1

HCID 54384183HCID 54384183, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 22.8 g of N'-(4-cyano-3-isopropyl- 5-isothiazolyl)-N,N-dimethylurea in 300 ml of benzene was added 83.3 g of phosphorous oxybromide. The solution was cooled to 0° and 14 ml (9.7 g) of triethylamine was added. The ice-bath was removed and the reaction mixture was heated under reflux overnight. The following day the reaction mixture was filtered through sintered glass. The filtrate was washed with two 200 ml portions of cold water and two 200 ml portions of saturated sodium bicarbonate solution. Two hundred milliliters of chloroform was added to aid in separation of the organic phase from the final wash. The separated organic phase was dried, then concentrated under reduced pressure. The residue was passed over a column of 300 grams of silica gel with chloroform as the eluant. The first ten 250 ml fractions were evaporated to produce a yellow solid, mp 93°-97°. The combined residues were recrystallized from 175 ml of cyclohexane to yield 13.8 g of N'-(4 -cyano-3-isopropyl-5-isothiazolyl)-N,N-dimethylbromoformamidine mp 92°-96°. The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. temperatureThe solution was cooled to 0°
  2. customThe ice-bath was removed
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux overnight
  5. filtrationThe following day the reaction mixture was filtered through sintered glass
  6. washThe filtrate was washed with two 200 ml portions of cold water and two 200 ml portions of saturated sodium bicarbonate solution
  7. additionTwo hundred milliliters of chloroform was added
  8. customto aid in separation of the organic phase from the
  9. washfinal wash
  10. customThe separated organic phase was dried
  11. concentrationconcentrated under reduced pressure
  12. customThe first ten 250 ml fractions were evaporated
  13. customto produce a yellow solid, mp 93°-97°
  14. customThe combined residues were recrystallized from 175 ml of cyclohexane

Sources & evidence

ORD record
ord-6c6466e999ce42939390c62581c18d6d
Source dataset
uspto-grants-1977_06
Patent number
US04032322

Reaction notes

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