HCID 11827930, compound → HCID 86758094, compound

HRID 991158Notes

Reaction equation

HRID 991158 reaction equation
[N-:1]=[N+:2]=[N-:3].[F:4][C:5]1[C:10]([B:11]([C:23]2[C:28]([F:29])=[C:27]([F:30])[C:26]([F:31])=[C:25]([F:32])[C:24]=2[F:33])[C:12]2[C:17]([F:18])=[C:16]([F:19])[C:15]([F:20])=[C:14]([F:21])[C:13]=2[F:22])=[C:9]([F:34])[C:8]([F:35])=[C:7]([F:36])[C:6]=1[F:37].[F:38][C:39]1[C:44]([B:45]([C:57]2[C:62]([F:63])=[C:61]([F:64])[C:60]([F:65])=[C:59]([F:66])[C:58]=2[F:67])[C:46]2[C:51]([F:52])=[C:50]([F:53])[C:49]([F:54])=[C:48]([F:55])[C:47]=2[F:56])=[C:43]([F:68])[C:42]([F:69])=[C:41]([F:70])[C:40]=1[F:71].[K+].[Cl-].[CH2:74]([NH+:92]([CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH2:110][CH3:111])[CH3:93])[CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH3:91]>ClCCl>[N-:1]=[N+:2]=[N-:3].[F:29][C:28]1[C:23]([B:11]([C:10]2[C:5]([F:4])=[C:6]([F:37])[C:7]([F:36])=[C:8]([F:35])[C:9]=2[F:34])[C:12]2[C:13]([F:22])=[C:14]([F:21])[C:15]([F:20])=[C:16]([F:19])[C:17]=2[F:18])=[C:24]([F:33])[C:25]([F:32])=[C:26]([F:31])[C:27]=1[F:30].[F:63][C:62]1[C:57]([B:45]([C:44]2[C:39]([F:38])=[C:40]([F:71])[C:41]([F:70])=[C:42]([F:69])[C:43]=2[F:68])[C:46]2[C:47]([F:56])=[C:48]([F:55])[C:49]([F:54])=[C:50]([F:53])[C:51]=2[F:52])=[C:58]([F:67])[C:59]([F:66])=[C:60]([F:65])[C:61]=1[F:64].[CH2:94]([NH+:92]([CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH3:91])[CH3:93])[CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101][CH2:102][CH2:103][CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH2:109][CH2:110][CH3:111]

Participants

4

Reactant 2

HCID 11827930HCID 11827930, compoundHCID 86758095HCID 86758095, compound

Product 1

HCID 86758094HCID 86758094, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Potassium bis(tris(pentafluorophenyl)borane)azide (1500.0 mg, 1.3573 mmol) and dioctadecylmethylammonium chloride (777.0 mg, 1.3573 mmol) were placed in a 50 mL flask. The solids were cooled to −78° C. and taken up in 20 mL of dichloromethane, added via syringe under argon counter-flow. As the stirred mixture warmed, the original solids dissolved and a fine precipitate of a colorless solid formed. The solid was removed by filtration and washed with two 5 mL portions of dichloromethane. The filtrate stripped under high vacuum, giving a colorless oil. Yield, 1646 mg, 75.33 percent.

Workup

  1. additionadded via syringe under argon counter-flow
  2. temperatureAs the stirred mixture warmed
  3. dissolutionthe original solids dissolved
  4. customa fine precipitate of a colorless solid formed
  5. customThe solid was removed by filtration
  6. washwashed with two 5 mL portions of dichloromethane
  7. customgiving a colorless oil
  8. customYield

Sources & evidence

ORD record
ord-714065ba94c24a16be590429244c9754
Source dataset
uspto-grants-2002_10
Patent number
US06462156B2

Reaction notes

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