Butyryl chloride → HCID 70511397, compound

HRID 1632316Notes

Reaction equation

HRID 1632316 reaction equation
Cl.[CH:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([OH:24])[CH:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:14])=[CH:8][CH:7]=1)([CH3:4])[CH3:3].[C:25]([Cl:30])(=[O:29])[CH2:26][CH2:27][CH3:28]>C(#N)C>[ClH:30].[C:25]([O:24][CH:12]([C:9]1[CH:10]=[CH:11][C:6]([S:5][CH:2]([CH3:4])[CH3:3])=[CH:7][CH:8]=1)[CH:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:14])(=[O:29])[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 30169122-(Octylamino)-1-{4-[(propan-2-yl)sulfanyl]phenyl}propan-1-ol--hydrogen chloride (1/1)

Product 1

HCID 70511397HCID 70511397, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture made of 10 gr (27 mmol) of 1-(4-isopropylthiophenyl)-2-n-octylamino-1-propanol hydrochloride and 11.4 gr (107 mmol) of butyryl chloride is heated at reflux temperature until a limpid solution is obtained. 10 ml of acetonitrile are added and reflux is maintained for about 2 hours. The solution so obtained is diluted with 40 ml of acetonitrile before being cooled. The white solid if filtered off. After recrystallisation from acetonitrile, the product weights 6.4 gr (14 mmol, 52%) and has a melting point of 104.1° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature until a limpid solution
  3. customis obtained
  4. temperaturereflux
  5. temperatureis maintained for about 2 hours
  6. customThe solution so obtained
  7. temperaturebefore being cooled
  8. filtrationThe white solid if filtered off
  9. customAfter recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-06ce6b5f8bc74c7d87b645015ce42fce
Source dataset
uspto-grants-1984_10
Patent number
US04474977

Reaction notes

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