Sodium Azide → HCID 54358027, compound

HRID 1583823Notes

Reaction equation

HRID 1583823 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@@H:18]([CH2:29]I)[O:17][C@@H:6]1[S:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C=O)C>[C:1]([O:4][C@H:5]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@@H:18]([CH2:29][N:31]=[N+:32]=[N-:33])[O:17][C@@H:6]1[S:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 54283487HCID 54283487, compound

Product 1

HCID 54358027HCID 54358027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 11 (8.0 g) and sodium azide (2.0 g) in DMF (100 ml) is heated with stirring for 24 hours at 85° C. (bath temperature). The solvent is evaporated in vacuo and the residue is partitioned between chloroform and water. The organic layer is separated and washed with water, dried, and evaporated to a thick syrup (7.2 g, 98%): [α]D27 +107±0.5° (C 1.0, chloroform).

Workup

  1. temperatureis heated
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is partitioned between chloroform and water
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. customevaporated to a thick syrup (7.2 g, 98%)

Sources & evidence

ORD record
ord-b55b50c173ec4a2aa9bafc4556258c58
Source dataset
uspto-grants-1985_11
Patent number
US04554349

Reaction notes

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