Sodium Azide → HCID 178501325, compound

HRID 355236Notes

Reaction equation

HRID 355236 reaction equation
C1(S(O[C@H:11]2[CH2:14][C@H:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12]2)(=O)=O)C=CC=CC=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C)P(N(C)C)(N(C)C)=O.O>[N:19]([C@@H:11]1[CH2:14][C@H:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12]1)=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 178501346HCID 178501346, compound

Product 1

HCID 178501325HCID 178501325, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
105 °C

Procedure

A solution of trans 3-carbomethoxycyclobutyl benzenesulfonate* (6.1 g, 22.6 mmol) in hexamethylphosphoramide (35 ml) was treated with sodium azide (289 g, 44.5 mmol) and stirred at 105° C. for 2.75 h. The reaction mixture was cooled to 23° C., diluted with water (350 ml) and extracted with ether (4×125 ml). The organic extracts were combined, washed with water (2×15 ml), dried over anhydrous magnesium sulfate and concentrated in vacuo to a slightly yellow liquid which was distilled under high vacuum; bp 66°-7° C. (0.6 mm); 2.8 g; 80%; ir (neat) νmax : 2100 (N3) and 1735 cm-1 (C=O); Hmr (CDCl3) δ: 40.34 (m, H-1), 3.7 (s, methyl) and 2.9-2.1 ppm (5H, 2H-2, H-3 and 2H-4).

Workup

  1. temperatureThe reaction mixture was cooled to 23° C.
  2. extractionextracted with ether (4×125 ml)
  3. washwashed with water (2×15 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo to a slightly yellow liquid which
  6. distillationwas distilled under high vacuum

Sources & evidence

ORD record
ord-2287e91aa18c47e69a826630e2355417
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

Loading…