Triethylamine → HCID 14054322, compound

HRID 1382861Notes

Reaction equation

HRID 1382861 reaction equation
[C:1]1([C:7]2[C:12]3[S:13][CH:14]=[CH:15][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.[CH2:19]([N:21](CC)[CH2:22]C)[CH3:20].CNCC.C1CCCCC1.C(O)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.S(Cl)(Cl)=O>[CH2:19]([N:21]([CH3:22])[C:16]([C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:12]2[S:13][CH:14]=[CH:15][C:11]=2[CH:10]=1)=[O:18])[CH3:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12219N-MethylethylamineHCID 14054310HCID 14054310, compoundHCID 21273355HCID 21273355, compound

Product 1

HCID 14054322HCID 14054322, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

The reaction is carried out as in Example 1, starting with 7-phenylbenzo[b]thiophene-5-carboxylic acid (3 g) in toluene (30 cc) and thionyl chloride (2.64 cc) and then triethylamine (5 cc) and N-methylethylamine (1.01 cc) in toluene (30 cc). After chromatography of the residue on silica gel using a cyclohexane:ethanol:ethyl acetate (90:5:5 by volume) mixture as the eluent, a residue is obtained, which is stirred overnight in 40°-60° petroleum spirit (50 cc). After filtering and drying, N-ethyl-N-methyl-7-phenylbenzo[b]thiophene-5-carboxamide (1.5 g), m.p. 93° C., is isolated.

Workup

  1. filtrationAfter filtering
  2. customdrying

Sources & evidence

ORD record
ord-ffc24fbc8d5e4b8faacd72db18470ca8
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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