Chlorosuccinimide → HCID 90418713, compound

HRID 2177331Notes

Reaction equation

HRID 2177331 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:13][OH:14])=[CH:4][CH:3]=1.C1C(=O)N([Cl:22])C(=O)C1>CN(C)C=O>[Cl:22][C:11]1[S:10][C:9]([CH2:13][OH:14])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 90418164HCID 90418164, compound

Product 1

HCID 90418713HCID 90418713, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Into a 50-mL round-bottom flask, was placed [3-(4-chlorophenyl)thiophen-2-yl]methanol (500 mg, 2.23 mmol, 1.00 equiv), N,N-dimethylformamide (10 mL), NCS (300 mg, 2.25 mmol, 1.01 equiv). The resulting solution was stirred for 2 h at 25° C. The reaction was then quenched by the addition of 20 ml of water. The resulting solution was extracted with 2×20 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×50 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with PE/EA (30/1-10/1). This resulted in 350 mg (55%) of [5-chloro-3-(4-chlorophenyl)thiophen-2-yl]methanol as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 20 ml of water
  3. extractionThe resulting solution was extracted with 2×20 mL of ethyl acetate
  4. washThe resulting mixture was washed with 3×50 mL of brine
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 350 mg (55%) of [5-chloro-3-(4-chlorophenyl)thiophen-2-yl]methanol as a white solid

Sources & evidence

ORD record
ord-3ce4ed60f352428896b0846db03a9493
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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