Cyanogen Bromide → HCID 18963188, compound

HRID 1707322Notes

Reaction equation

HRID 1707322 reaction equation
[C:1](Br)#[N:2].[F:4][C:5]([F:48])([F:47])[C:6]([C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][C:37]=2[C:43]([F:46])([F:45])[F:44])=[CH:31][CH:30]=1)([C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=2[C:25]([F:28])([F:27])[F:26])=[CH:13][CH:12]=1)[C:7]([F:10])([F:9])[F:8].C[C:50]([N:52](C)C)=O>C(=O)(O)[O-].[Na+].O>[F:4][C:5]([F:47])([F:48])[C:6]([C:29]1[CH:30]=[CH:31][C:32]([O:35][C:36]2[CH:41]=[CH:40][C:39]([NH:42][C:1]#[N:2])=[CH:38][C:37]=2[C:43]([F:44])([F:45])[F:46])=[CH:33][CH:34]=1)([C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:50]#[N:52])=[CH:20][C:19]=2[C:25]([F:28])([F:26])[F:27])=[CH:15][CH:16]=1)[C:7]([F:10])([F:9])[F:8]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 31374Dimethylacetamide2×HCID 11388190HCID 11388190, compound

Product 1

HCID 18963188HCID 18963188, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Bromocyanogen in an amount of 63.5 g, and 25.2 g of sodium bicarbonate were dissolved in a mixed solvent of 75 ml of water and 50 ml of dimethylacetamide with sufficient stirring (in a cooled state). To the resulting solution, a solution obtained by dissolving 98.1 g of 1,1,1,3,3,3-hexafluoro-2,2-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]propane in 300 ml of dimethylacetamide was added dropwise in about 4 hours while maintaining the cooled state at 0° to 10° C. After dropwise addition, aging was conducted for 12 hours. The resulting reaction solution was dropped in 1000 ml of water with stirring to deposit a pale yellow precipitate. The precipitate was separated by filtration with suction. The resulting precipitate was charged into 1000 ml of water again, washed with water, filtered again and washed with water. The resulting filtered solid was subjected to filtration under reduced pressure (drying conditions; temperature 30° C., pressure 10 mmHg, period 12 hours) to yield 104.8 g of crystals of the objective compound, 1,1,1,3,3,3-hexafluoro-2,2-bis[4-(4-cyanoamino-2-trifluoromethylphenoxy)phenyl]propane (yield 98.2%). The resulting compound (p-HFCTP-2) had a melting point of 55° to 60° C. IR spectrum of said compound is shown in FIG. 4 and NMR spectrum of said compound is shown in FIG. 3.

Workup

  1. customTo the resulting solution, a solution obtained
  2. additionwas added dropwise in about 4 hours
  3. temperaturewhile maintaining the cooled state at 0° to 10° C
  4. additionAfter dropwise addition
  5. customThe resulting reaction solution
  6. stirringwith stirring
  7. customThe precipitate was separated by filtration with suction
  8. additionThe resulting precipitate was charged into 1000 ml of water again
  9. washwashed with water
  10. filtrationfiltered again
  11. washwashed with water
  12. filtrationThe resulting filtered solid
  13. filtrationwas subjected to filtration under reduced pressure (drying conditions; temperature 30° C., pressure 10 mmHg, period 12 hours)

Sources & evidence

ORD record
ord-eaf0c52701d14e47a007de52af45ea82
Source dataset
uspto-grants-1994_10
Patent number
US05352762

Reaction notes

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