Phosgene → HCID 13363520, compound

HRID 1788942Notes

Reaction equation

HRID 1788942 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:5]2[O:6][CH2:7][O:8][CH2:9][C:4]=2[CH:3]=1.[C:15](Cl)(Cl)=[O:16].C(N(CC)CC)C.[F:26][CH2:27][CH2:28][OH:29]>C1(C)C=CC=CC=1>[CH2:13]([O:12][C:10]1[C:5]2[O:6][CH2:7][O:8][CH2:9][C:4]=2[CH:3]=[C:2]([NH:1][C:15](=[O:16])[O:29][CH2:28][CH2:27][F:26])[CH:11]=1)[CH3:14]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 97372-FluoroethanolHCID 20189638HCID 20189638, compound

Product 1

HCID 13363520HCID 13363520, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of 6-amino-8-ethoxy-1,3-benzodioxane (1.95 g) in toluene (20 ml), a toluene solution containing phosgene (10 g) was dropwise added at 10° to 20° C. The resultant mixture was heated gradually and, after being refluxed for 30 minutes, cooled to room temperature. The solvent was removed in vacuo, whereby crude 8-ethoxy-1,3-benzodioxan-6-ylisocyanate was obtained. This crude substance was dropwise added to a toluene solution (50 ml) containing triethylamine (1.0 g) and 2-fluoroethanol (0.70 g) at room temperature. The resultant mixture was allowed to stand at room temperature for 12 hours, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as the eluent to give 2-fluoroethyl N-(8-ethoxy-1,3-benzodioxan-6-yl)carbamate (Compound No. 10) (2.31 g) in a yield of 80.9%. M.P., 154° -154.5° C.

Workup

  1. additionwas dropwise added at 10° to 20° C
  2. temperatureafter being refluxed for 30 minutes
  3. customThe solvent was removed in vacuo
  4. customwhereby crude 8-ethoxy-1,3-benzodioxan-6-ylisocyanate was obtained
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. additiona mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-5eb2f821488b423cbb3ed018620cc075
Source dataset
uspto-grants-1987_08
Patent number
US04686232

Reaction notes

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