Phenylacetyl chloride → HCID 19896890, compound

HRID 1196957Notes

Reaction equation

HRID 1196957 reaction equation
[CH2:1]([S:8]NC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([CH2:22][C:23](Cl)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([N:28]([CH2:31][CH3:32])CC)C>C(Cl)(Cl)Cl.CCCCCC>[CH2:1]([S:8][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:22][C:23]([NH:28][C:31]1[CH:32]=[CH:4][CH:3]=[CH:2][CH:1]=1)=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 54312060(Benzylthio)aniline

Product 1

HCID 19896890HCID 19896890, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8058HexaneSolvent

Procedure

(Benzylthio)aniline (21.5 g, 0.1 mol) (the preparation of which has been described in Example 1 of U.S. Pat. No. 3,378,586) was reacted with 13.4 ml (0.1 mol) of phenylacetyl chloride in 135 ml of chloroform in the presence of 14.0 ml (0.1 mol) of triethylamine in the manner described under Example 1, part B, to give a solid residue. The latter was redissolved in 35 ml of warm chloroform and diluted with 150 ml of hexane. On seeding and rubbing, a crystalline solid gradually separated. After cooling overnight, the colorless solid was filtered, washed with hexane, and air-dried (22.3 g), m.p. 81°-83°. Following recrystallization from 350 ml of hexane, the title A material weighed 20.8 g, m.p. 82°-84°.

Workup

  1. customto give a solid residue
  2. customOn seeding and rubbing, a crystalline solid gradually separated
  3. temperatureAfter cooling overnight
  4. filtrationthe colorless solid was filtered
  5. washwashed with hexane
  6. customair-dried (22.3 g), m.p. 81°-83°
  7. customrecrystallization from 350 ml of hexane

Sources & evidence

ORD record
ord-544668cb70c541e3b8bcd1baf705873e
Source dataset
uspto-grants-1992_05
Patent number
US05116851

Reaction notes

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