2,4-Dichlorobenzoyl chloride → HCID 23311300, compound

HRID 745998Notes

Reaction equation

HRID 745998 reaction equation
[N:1]1([CH2:6][CH:7]([OH:16])[CH2:8][S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>N1C=CC=CC=1.O>[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[C:20]([O:16][CH:7]([CH2:8][S:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:21]

Participants

5

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 13688950HCID 13688950, compound

Product 1

HCID 23311300HCID 23311300, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A mixture of 1-(1-imidazolyl)-3-phenylthiopropan-2-ol and 5 g (0.213 mole), in pyridine (15 ml) was cooled in an ice and water bath; then 4.9 g [3.3 ml (0.0235 mole)] 2,4-dichlorobenzoyl chloride was added dropwise. The reaction mixture was allowed to warm to room temperature and then stirred overnight. The resulting mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with a sodium bicarbonate solution, then several times with water and once with brine, dried, treated with activated charcoal, filtered and concentrated to give a brown gum (8.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with a sodium bicarbonate solution
  3. dry with materialseveral times with water and once with brine, dried
  4. additiontreated with activated charcoal
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-330ef947b4364c4dafbebc7cc204d4ce
Source dataset
uspto-grants-1986_07
Patent number
US04602030

Reaction notes

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