Diethylamine → HCID 14054337, compound

HRID 1382856Notes

Reaction equation

HRID 1382856 reaction equation
[C:1]1([C:7]2[C:15]3[CH:14]=[CH:13][S:12][C:11]=3[CH:10]=[C:9]([C:16]([OH:18])=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH2:23]([N:25](CC)[CH2:26][CH3:27])[CH3:24].C(NCC)C>C1(C)C=CC=CC=1.C1CCCCC1.C(OCC)(=O)C>[CH2:23]([N:25]([CH2:26][CH3:27])[C:16]([C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[CH:14]=[CH:13][S:12][C:11]=2[CH:10]=1)=[O:18])[CH3:24]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 13637980HCID 13637980, compound

Product 1

HCID 14054337HCID 14054337, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

The reaction is carried out as in Example 1, starting with 4-phenylbenzo[b]thiophene-6-carboxylic acid (4 g) and thionyl chloride (3.5 cc) in toluene (40 cc) and then adding triethylamine (13.25 cc) and diethylamine (1.6 cc) in toluene (40 cc). After chromatography of the residue on silica gel using a cyclohexane:ethyl acetate (50:50 by volume) mixture as the eluent and then stirring the product collected in 40°-60° petroleum spirit (30 cc) and filtering, N,N-diethyl-4-phenylbenzo[b]thiophene-6-carboxamide (2.55 g), m.p 60° C. is isolated.

Workup

  1. customcollected in 40°-60° petroleum spirit (30 cc)
  2. filtrationfiltering

Sources & evidence

ORD record
ord-2fb002b369e94b4c8ce2e47fcc35756d
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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