3-Chloro-1-propanol → HCID 20246947, compound

HRID 1589428Notes

Reaction equation

HRID 1589428 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.Cl[CH2:8][CH2:9][CH2:10][OH:11]>[OH-].[Na+]>[OH:11][CH2:10][CH2:9][CH2:8][N:3]1[C:2]([NH2:1])=[N:6][N:5]=[N:4]1.[OH:11][CH2:10][CH2:9][CH2:8][N:4]1[N:5]=[N:6][C:2]([NH2:1])=[N:3]1

Participants

5

Reactant 2

HCID 123133-Chloro-1-propanolHCID 178509299HCID 178509299, compound

Product 2

HCID 20246947HCID 20246947, compoundHCID 20246948HCID 20246948, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

5-Aminotetrazole (2.1 g.) and 3-chloropropanol (2.1 ml.) were added to aqueous sodium hydroxide (1 g. in 20 ml.) and the mixture heated at 90° for 18 hours. The resulting solution was evaporated and the residue extracted with hot EtOH. The EtOH extracts were evaporated and the residue extracted with EtOAc to give a colourless oil which was a mixture of isomers. These were separated on a column of silica gel using EtOAc/MeOH/aqueous ammonia (s.g. 0.880) 6:1:1 v/v/v as eluant to give 1-(3-hydroxypropyl)-5-aminotetrazole as a white solid (0.2 g.) and 2-(3-hydroxypropyl)-5-aminotetrazole as a gum (1.0 g.).

Workup

  1. temperaturethe mixture heated at 90° for 18 hours
  2. customThe resulting solution was evaporated
  3. extractionthe residue extracted with hot EtOH
  4. customThe EtOH extracts were evaporated
  5. extractionthe residue extracted with EtOAc
  6. customto give a colourless oil which
  7. additiona mixture of isomers
  8. customThese were separated on a column of silica gel

Sources & evidence

ORD record
ord-832d9a1a905340669799a42fb880dd59
Source dataset
uspto-grants-1986_02
Patent number
US04570000

Reaction notes

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