Hydrogen Bromide → HCID 178420440, compound

HRID 1649377Notes

Reaction equation

HRID 1649377 reaction equation
Br.C([N:5]1[C:9]([SH:10])=[N:8][N:7]=[N:6]1)C#C.Cl.N([O-])=O.[Na+].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH:22]([S:10][C:9]1[NH:5][N:6]=[N:7][N:8]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 1140TolueneHCID 23668193Sodium NitriteHCID 178456704HCID 178456704, compound

Product 1

HCID 178420440HCID 178420440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of the crude product of 3-benzhydrylisothiosemicarbazide hydrobromide from (1) above, water (2.3 l), conc. hydrochloric acid (126 g) and toluene (900 ml) was dropwise added a solution of sodium nitrite (83.5 g) in water (200 ml) and the resulting mixture was stirred for 1.5 hours at 10° to 15° C. The reaction mixture was extracted with ethyl acetate. The organic layer was added to water (1 l) and adjusted to pH 9.5 with 4 N aqueous solution of sodium hydroxide. The separated aqueous layer was then adjusted to pH 2.5 with 10% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried and evaporated to give a residue, which was washed with a mixture of n-hexane and isopropyl ether (2:1) and air-dried to give 5-benzhydrylthio-1H-tetrazole (127.22 g), mp. 132° to 134° C.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. additionThe organic layer was added to water (1 l)
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. customdried
  6. customevaporated
  7. customto give a residue, which
  8. washwas washed with a mixture of n-hexane and isopropyl ether (2:1)
  9. customair-dried

Sources & evidence

ORD record
ord-992dffed36724359ba9c93e6adc3b6b7
Source dataset
uspto-grants-1983_11
Patent number
US04416879

Reaction notes

Loading…