Imidazole → HCID 86738424, compound

HRID 1156401Notes

Reaction equation

HRID 1156401 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.[O:43]=[C:44]=[N:45][CH:46]1[CH2:55][C:54]([CH3:57])([CH3:56])[CH2:53][C:48]([CH3:58])([CH2:49][N:50]=[C:51]=[O:52])[CH2:47]1.[N-]=C=O>O1CCCC1>[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[O:43]=[C:44]=[N:45][CH:46]1[CH2:55][C:54]([CH3:57])([CH3:56])[CH2:53][C:48]([CH3:58])([CH2:49][N:50]=[C:51]=[O:52])[CH2:47]1

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 105034Isocyanate2×HCID 169132Isophorone diisocyanate2×HCID 9809426Di-n-butyldilauryltin

Product 1

HCID 86738424HCID 86738424, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a three-neck flask, provided with a magnetic stirrer, thermometer, and dropping funnel, there was placed 17.1 grams (0.25 moles) imidazole, 75 ml tetrahydrofuran, and 0.1 gram dibutyl tin dilaurate. After this material was mixed and the imidazole dissolved, 27.9 grams (0.125 moles) of isophorone diisocyanate was added dropwise while keeping the temperature between about 18°-25° C. with an ice water bath. After the isophorone diisocyanate was added, the solution was stirred for two hours and then allowed to stand for about a 12-hour period at room temperature (70° F). Isocyanate analysis showed that all of the isocyanate had reacted. The product was recovered by flashing the tetrahydrofuran at 55° C. under vacuum and then drying by placing the solids in a vacuum oven at 60° C. About 44 grams of isophorone diisocyanate blocked imidazole product was recovered.

Workup

  1. customIn a three-neck flask, provided with a magnetic stirrer
  2. additionAfter this material was mixed
  3. custombetween about 18°-25° C.
  4. customto stand for about a 12-hour period at room temperature
  5. custom(70° F)
  6. customhad reacted
  7. customThe product was recovered
  8. customat 55° C.
  9. customdrying
  10. customat 60° C
  11. customwas recovered

Sources & evidence

ORD record
ord-1e34bbbfc51842529c15da33b17f05c2
Source dataset
uspto-grants-1982_06
Patent number
US04335228

Reaction notes

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