Ammonium Chloride → HCID 178506188, compound

HRID 1606564Notes

Reaction equation

HRID 1606564 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][CH:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:8]#[N:9].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>CN(C)P(N(C)C)(N(C)C)=O>[F:21][C:2]([F:20])([F:1])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[O:6][CH:7]([C:8]1[NH:24][N:23]=[N:22][N:9]=1)[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22767844HCID 22767844, compound

Product 1

HCID 178506188HCID 178506188, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of (3-trifluoromethylphenoxy) (4-chlorophenyl)acetonitrile (10.68 g.), sodium azide (2.40 g.), ammonium chloride (1.98 g.) and hexamethylphosphoramide (85 ml.) is stirred at 60°-63°C. overnight (19 hours). The reaction mixture is cooled, poured into one liter of ice water containing 25 ml. of concentrated hydrochloric acid and this solution is extracted with 5 × 100 ml. of ether. The ether extracts are combined, extracted with water and dried over sodium sulfate. The ether solution is filtered, the ether is evaporated in vacuo and the residue is crystallized by trituration with methylcyclohexane. Recrystallization from a butyl chloride and methylcyclohexane mixture (about 1 to 1) affords 5-[α-(3-trifluoromethylphenoxy)-4-chlorobenzyl]tetrazole, m.p. 124.5°-126.5°C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionof concentrated hydrochloric acid and this solution is extracted with 5 × 100 ml
  3. extractionextracted with water
  4. dry with materialdried over sodium sulfate
  5. filtrationThe ether solution is filtered
  6. customthe ether is evaporated in vacuo
  7. customthe residue is crystallized by trituration with methylcyclohexane
  8. customRecrystallization from a butyl chloride and methylcyclohexane mixture (about 1 to 1)

Sources & evidence

ORD record
ord-d4f12e9187024ac387654f5e85f6b6b8
Source dataset
uspto-grants-1976_04
Patent number
US03953465

Reaction notes

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