p-Chlorophenacyl bromide → HCID 22496401, compound

HRID 1816178Notes

Reaction equation

HRID 1816178 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[S:11])=[CH:5][CH:4]=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=O.CCN(C(C)C)C(C)C>C(O)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:12]=[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:14])=[CH:8][CH:7]=3)[S:11][CH:16]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 68303p-Chlorophenacyl bromideHCID 81531DiisopropylethylamineHCID 2777727N-[4-(Trifluoromethyl)phenyl]thiourea

Product 1

HCID 22496401HCID 22496401, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Trifluoromethylphenyl)thiourea (5.00 g; 22.7 mmol) was dissolved in ethanol (45 mL) by gentle heating. Then, α-bromo-p-chloroacetophenone (5.30 g; 22.70 mmol) and DIPEA (3.22 g; 24.9 mmol) was added. The resulting solution was stirred for 16 hours at ambient temperature. The mixture was then concentrated in vacuo, and the residue dissolved in ethyl acetate. The DIPEA hydrobromide, which crystallized out of solution, was removed by filtration. The filtrate was washed with water (2×50 mL) and brine (50 mL), and dried over anhydrous sodium sulphate. The solvent was removed by rotary evaporation to give 7.00 g (93%) of [4-(4-chlorophenyl)thiazol-2-yl]-(4-trifluoromethylphenyl)amine as an oil. The material was pure enough for use in the next step (a crystalline sample can be obtained by re-crystallization in heptane).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. customThe DIPEA hydrobromide, which crystallized out of solution
  4. customwas removed by filtration
  5. washThe filtrate was washed with water (2×50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-59ebc67e009047728677944530ebbf39
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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