Water → HCID 10615659, compound

HRID 423438Notes

Reaction equation

HRID 423438 reaction equation
C(N(CC)[C:4]([C:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1)=[O:5])C.[CH2:17]([Li])[CH2:18][CH2:19][CH3:20].[OH2:22].C(Cl)(Cl)Cl>C(OCC)C>[CH:17]1[C:6]2[C:7]3[C:14](=[O:22])[C:10]4[S:9][C:8]5[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=5[C:6]=4[C:4](=[O:5])[C:8]=3[S:9][C:10]=2[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 40103909HCID 40103909, compoundHCID 178418339Butyllithium

Product 1

HCID 10615659HCID 10615659, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
3 °C

Procedure

To a solution of benzo[b]thiophene-3-carboxylic acid diethylamide (14.0 g, 60 mmol) in diethyl ether (120 ml) is cooled to −78° C. Under an inert atmosphere a solution of n-butyllithium in hexanes (41.3 ml 1.6 N solution, 66 mmol) is then added within 15 minutes. There is a slight increase of the temperature by 3° C., and the mixture is allowed to stir for another 10 minutes at −78 . . . −75° C. Then the mixture is allowed to warm to ambient temperature. After ca. 1.5 hours a reddish brown suspension is formed which is stirred for another 17 hours. Then water (150 ml) is carefully added to the mixture and also chloroform (50 ml). The mixture is stirred rapidly for 15 minutes, and the solid is filtered off, washed with water, dried and recrystallized from DMSO (50 ml) to give the product as orange brown needles mp=315° C.

Workup

  1. custom−75° C
  2. temperatureto warm to ambient temperature
  3. customAfter ca. 1.5 hours a reddish brown suspension is formed which
  4. stirringis stirred for another 17 hours
  5. stirringThe mixture is stirred rapidly for 15 minutes
  6. filtrationthe solid is filtered off
  7. washwashed with water
  8. customdried
  9. customrecrystallized from DMSO (50 ml)

Sources & evidence

ORD record
ord-031f5eae7e0148348350a78795f6932f
Source dataset
uspto-grants-2012_01
Patent number
US08101776B2

Reaction notes

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