Chloroacetyl chloride → HCID 178520783, compound

HRID 864827Notes

Reaction equation

HRID 864827 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]([CH2:12][C:13]1[NH:17][N:16]=[N:15][N:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>ClCCCl>[Cl:18][CH2:19][C:20]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:12][C:13]2[NH:17][N:16]=[N:15][N:14]=2)=[CH:7][CH:8]=1)=[O:21]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178420518HCID 178420518, compound

Product 1

HCID 178520783HCID 178520783, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Aluminium chloride (30.3 g) was added to a stirred mixture of the product of step (i) above (10 g) and chloroacetyl chloride (19.3 g) in dry 1,2-dichloroethane and stirring continued overnight. The mixture was concentrated to about half volume on the steam bath, cooled and added to an ice/hydrochloric acid mixture. After stirring for 15 minutes the solid was collected and, on recrystallisation from methanol/water, gave 5-(4-chloroacetylphenoxymethyl)tetrazole, 7.5 g: m.p. 194°-196° C.; NMR (d6DMSO) δ7.99 (2H, d), 7.20 (2H, d), 5.61 (2H, s), 5.11 (2H, s); m/e 251 (M-H)-, 1 Cl pattern; calculated for C10H9ClN4O2 : C, 47.5; H, 3.6; N, 22.2. found: C, 47.3; H, 3.7; N, 22.2%.

Workup

  1. concentrationThe mixture was concentrated to about half volume on the steam bath
  2. temperaturecooled
  3. additionadded to an ice/hydrochloric acid mixture
  4. stirringAfter stirring for 15 minutes the solid
  5. customwas collected and, on recrystallisation from methanol/water

Sources & evidence

ORD record
ord-84ec8f3b44344fc599b5b6f3ddf8a86d
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

Loading…