Water → HCID 70978147, compound

HRID 2281050Notes

Reaction equation

HRID 2281050 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:25]=[CH:24][C:16]3[N:17]([CH2:20][CH:21]4[CH2:23][CH2:22]4)[N:18]=[N:19][C:15]=3[C:14]=2[C:26]([F:29])([F:28])[F:27])=[CH:9][CH:8]=1)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+].O>CS(C)=O>[N:30]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:25]=[CH:24][C:16]3[N:17]([CH2:20][CH:21]4[CH2:23][CH2:22]4)[N:18]=[N:19][C:15]=3[C:14]=2[C:26]([F:29])([F:28])[F:27])=[CH:9][CH:8]=1)=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86711981HCID 86711981, compound

Product 1

HCID 70978147HCID 70978147, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-[1-(Cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazole-5-yl]benzyl methanesulfonate (185 mg, 0.435 mmol) was dissolved in dimethylsulfoxide, treated with sodium azide (141 mg, 2.17 mmol, 5 equiv) and placed into a preheated oil bath at 70° C. for 30 minutes. The mixture was cooled to ambient temperature, poured into water (150 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39f5db037c814585ac5e560d19bab46a
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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