1,4-Dioxane → 2-[(cyclohexyloxy)methylphenyl}-N-(diphenylmethylene)-1,3-thiazol-2-amine

HRID 1182383Notes

Reaction equation

HRID 1182383 reaction equation
Br[C:2]1[S:6][C:5]([N:7]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][CH:3]=1.O1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[CH:23]1([O:24][CH2:25][C:26]2[CH:16]=[CH:15][CH:8]=[CH:9][C:10]=2[C:5]2([N:7]=[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:4][CH:3]=[CH:2][S:6]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:22]1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 112215925-Bromo-N-(diphenylmethylene)-2-thiazolamine

Product 1

HCID 1317266562-[(cyclohexyloxy)methylphenyl}-N-(diphenylmethylene)-1,3-thiazol-2-amine

Procedure

24 g of tripotassium phosphate trihydrate, 16.7 g of 2-[(cyclohexyloxy)methyl]phenylboronic acid, obtained in step 1.2, and 2 g of tetrakis(triphenylphosphine)palladium(0) are successively introduced into 17 g of 5-bromo-N-(diphenylmethylene)-1,3-thiazol-2-amine, obtained in step 1.3, in suspension in 250 ml of 1,4-dioxane, and the mixture is kept at 60° C. for 18 hours. The reaction medium is evaporated to dryness, the residue is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a silica gel column, eluting with dichloromethane to give 37.2 g of a yellow oil.

Workup

  1. customThe reaction medium is evaporated to dryness
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a silica gel column
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-06bc02a6a7594c32a05baea5dea8a363
Source dataset
uspto-grants-2007_10
Patent number
US07288659B2

Reaction notes

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