Thionyl Chloride → HCID 22258070, compound

HRID 1610992Notes

Reaction equation

HRID 1610992 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:25](O)[C:26]([OH:28])=[O:27].[NH:30]1C2C=CC=CC=2N=N1.S(Cl)(Cl)=O.[N-]=[N+]=[N-].[Na+]>C(Cl)Cl.O>[NH2:30][CH:25]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:10]=1[O:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:26]([OH:28])=[O:27]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 9932554HCID 9932554, compoundHCID 178418385HCID 178418385, compound

Product 1

HCID 22258070HCID 22258070, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of Example 1 Part B compound (1.009 g, 2.19 mmol) in CH2Cl2 (20 mL) under argon at room temperature was added a solution prepared from benzotriazole (570 mg, 4.8 mmol) and thionyl chloride (570 mg, 4.8 mmol) in CH2Cl2 (5 mL) over 2 min. The reaction mixture was stirred for 90 min, then diluted with water and extracted twice with CH2Cl2. The extracts were combined, washed once with water, once with 0.5 M NaOH (25 mL) and once with brine, dried (MgSO4) and evaporated. The residuum was immediately dissolved in DMF (8 mL), treated with sodium azide (570 mg, 8.8 mmol) and stirred at room temperature under argon for 1 h. The reaction mixture was quenched with water and extracted twice with Et2O. The extracts were combined, washed twice with water, once with brine dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 657 mg (62% yield). LC/MS gave the correct molecular ion [(M+H)+=486] for the desired compound.

Workup

  1. extractionextracted twice with CH2Cl2
  2. washwashed once with water, once with 0.5 M NaOH (25 mL) and once with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residuum was immediately dissolved in DMF (8 mL)
  6. stirringstirred at room temperature under argon for 1 h
  7. customThe reaction mixture was quenched with water
  8. extractionextracted twice with Et2O
  9. washwashed twice with water, once with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-62a8df937ee24168b41999f5bd28fb48
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

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