Sodium Azide → 7-(2-azidoacetyl)-4-hydroxybenzo[d]thiazol-2(3H)-one

HRID 1689177Notes

Reaction equation

HRID 1689177 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:13]2[S:12][C:11](=[O:14])[NH:10][C:9]=2[C:8]([OH:15])=[CH:7][CH:6]=1)=[O:4].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O>[N:16]([CH2:2][C:3]([C:5]1[C:13]2[S:12][C:11](=[O:14])[NH:10][C:9]=2[C:8]([OH:15])=[CH:7][CH:6]=1)=[O:4])=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 579893277-(2-Chloroacetyl)-4-hydroxybenzo[d]thiazol-2(3H)-one

Product 1

HCID 866367477-(2-azidoacetyl)-4-hydroxybenzo[d]thiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(2-Chloro-acetyl)-4-hydroxy-3H-benzothiazol-2-one (example 1, step a) (331 g) was dissolved in N,N-dimethylformamide (1800 mL) and stirred in an ice bath for 10 minutes. Sodium azide (88.3 g) was added portionwise over 15 minutes. The reaction was stirred for 72 hours and then the reaction mixture was divided into 3 equal portions and each quenched separately into ice and water (2.5 L). The solid was filtered off and washed with water (1 L) and re-suspended in acetonitrile (1.5 L). The solvent was evaporated and a further portion of acetonitrile (1 L) added and solvent evaporated again to dry the product. Diethyl ether (1.5 L) was added and the mixture stirred to achieve an homogeneous suspension. The solid was collected and dried in vacuo at 35° C. for 24 hours to give the subtitled compound. Yield 285 g.

Workup

  1. stirringThe reaction was stirred for 72 hours
  2. customeach quenched separately into ice and water (2.5 L)
  3. filtrationThe solid was filtered off
  4. washwashed with water (1 L)
  5. customThe solvent was evaporated
  6. additiona further portion of acetonitrile (1 L) added
  7. customsolvent evaporated again
  8. customto dry the product
  9. additionDiethyl ether (1.5 L) was added
  10. stirringthe mixture stirred
  11. customThe solid was collected
  12. customdried in vacuo at 35° C. for 24 hours

Sources & evidence

ORD record
ord-2f1e2aaa1413473cbb9e21127360c926
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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