Water → HCID 20043672, compound

HRID 1761937Notes

Reaction equation

HRID 1761937 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)(O)[CH:11]([N:13]2[N:17]=[N:16][CH:15]=[N:14]2)[CH3:12])=[CH:6][CH:5]=1.C(N(S(F)(F)[F:38])CC)C.[OH-].[K+].O>ClCCl>[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)([F:38])[CH:11]([N:13]2[N:17]=[N:16][CH:15]=[N:14]2)[CH3:12])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 123472(Diethylamino)sulfur trifluoride2×HCID 20042590HCID 20042590, compound

Product 1

HCID 20043672HCID 20043672, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-bis(4-trifluoromethoxyphenyl)-2-(1,2,3,4-2H-tetrazol-2-yl)propan-1-ol (3.5 g) prepared as described in Example 3 in dichloromethane (50 cm3) was added dropwise to a stirred solution of diethylaminosulphurtrifluoride (1.51 g) kept at a temperature of -70° C. under a nitrogen atmosphere. After 1 hour a further quantity of diethylaminosulphurtrifluoride (1.5 g) was added and the mixture stirred for 18 hours at the ambient temperture, during which time any vapours emitted were vented through a column of potassium hydroxide pellets. Water (30 cm3) was added carefully to the mixture, the organic layer separated and washed with more water (3×30 cm3), dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent under reduced pressure. The residual oil (4.5 g) was purified by hplc using a silica gel column eluted with a mixture of hexane (5 parts by volume and ethylacetate (1 part by volume) to yield 1,1-bis(4-trifluoromethoxyphenyl)-1-fluoro- 2-(1,2,3,4-2H-tetrazol-2-yl)propane as an oil (3.19 g) which crystallised on standing (mp. 68°-70° C.).

Workup

  1. customkept at a temperature of -70° C. under a nitrogen atmosphere
  2. customthe organic layer separated
  3. washwashed with more water (3×30 cm3)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated by evaporation of the solvent under reduced pressure
  6. customThe residual oil (4.5 g) was purified by hplc
  7. washeluted with a mixture of hexane (5 parts by volume and ethylacetate (1 part by volume)

Sources & evidence

ORD record
ord-5d64a036e3da4576825bc0f8e00b3731
Source dataset
uspto-grants-1989_05
Patent number
US04829074

Reaction notes

Loading…