Sodium Azide → HCID 86599109, compound

HRID 2115990Notes

Reaction equation

HRID 2115990 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([Cl:27])[CH:20]=[C:21]([C:22]4[CH:26]=[CH:25][S:24][CH:23]=4)[C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:28]=[N+:29]=[N-:30].[Na+]>CS(C)=O.O.C(OCC)C>[N:28]([CH2:12][CH:13]1[CH2:17][C:16]2[CH:18]=[C:19]([Cl:27])[CH:20]=[C:21]([C:22]3[CH:26]=[CH:25][S:24][CH:23]=3)[C:15]=2[O:14]1)=[N+:29]=[N-:30]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 86599107HCID 86599107, compound

Product 1

HCID 86599109HCID 86599109, compoundYield 83.4%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (±)-(5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate (4.5 g, 10.69 mmol) in dimethylsulfoxide (150 mL) was added sodium azide (3.6 g, 55.38 mmol) and the reaction mixture was heated to 70° C. and allowed to stir for 6 h. The reaction mixture was cooled to room temperature and diluted with water (300 mL) and diethyl ether (200 mL). The aqueous layer was separated and extracted with diethyl ether (200 mL). The combined organic layers were washed with water (3×200 mL), saturated aqueous sodium chloride (100 mL), dried (magnesium sulfate), and the solvent removed in vacuo to afford 2.6 g (83%) of (±)-2-(azidomethyl)-5-chloro-7-thien-3-yl-2,3-dihydro-1-benzofuran as a white solid. mp 50-52° C.; Anal. calcd. for C13H10ClN3OS: C, 53.52; H, 3.45; N, 14.40. Found: C, 53.50; H, 3.33; N, 14.26.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with diethyl ether (200 mL)
  4. washThe combined organic layers were washed with water (3×200 mL), saturated aqueous sodium chloride (100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f1540534433d421cba305a82608a0cd2
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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