Ethyl isocyanate → HCID 10336406, compound

HRID 1110078Notes

Reaction equation

HRID 1110078 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]2[C:5]([C:6]([Cl:17])=[C:7]([O:13][CH2:14][CH2:15][CH3:16])[O:8][C:9]2=[O:10])=[CH:4][CH:3]=1.[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19]>C1COCC1>[CH2:18]([NH:20][C:21]([NH:1][C:2]1[CH:12]=[C:11]2[C:5]([C:6]([Cl:17])=[C:7]([O:13][CH2:14][CH2:15][CH3:16])[O:8][C:9]2=[O:10])=[CH:4][CH:3]=1)=[O:22])[CH3:19]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 15022011HCID 15022011, compound

Product 1

HCID 10336406HCID 10336406, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized by the reaction of an equimolar amount of 7-amino-4-chloro-3-propoxyisocoumarin and ethyl isocyanate in small amount of dry THF. The reaction mixture was stirred at r. t. for a few days. During this time the yellow crystals slowly crystallized out. After filtration, the compoumds were recrystallized once more from THF-pentane, yield 45%; mp 189°-191° C.; TLC, Rf =0.43 (CH3Cl:MeOH=9:1); MS, m/e 324 (M+). Anal. Calc. for C15H17O4N2Cl: C, 55.42; H, 5.23. Found: C, 55.31; H, 5.28.

Workup

  1. waitfor a few days
  2. customDuring this time the yellow crystals slowly crystallized out
  3. filtrationAfter filtration
  4. customthe compoumds were recrystallized once more from THF-pentane, yield 45%

Sources & evidence

ORD record
ord-48e0ce39c2da49ab8c852a1e6385ee3b
Source dataset
uspto-grants-1994_06
Patent number
US05324648

Reaction notes

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