Triethylamine → HCID 14054341, compound

HRID 1382863Notes

Reaction equation

HRID 1382863 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[CH:16]=[CH:15][S:14][C:13]=3[CH:12]=[C:11]([C:18]([OH:20])=O)[CH:10]=2)=[CH:5][CH:4]=1.[CH2:21]([N:23](CC)[CH2:24][CH3:25])[CH3:22]>C1(C)C=CC=CC=1.S(Cl)(Cl)=O.C(NCC)C>[CH2:21]([N:23]([CH2:24][CH3:25])[C:18]([C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:17]2[CH:16]=[CH:15][S:14][C:13]=2[CH:12]=1)=[O:20])[CH3:22]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 13637982HCID 13637982, compound

Product 1

HCID 14054341HCID 14054341, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 8021DiethylamineSolventHCID 24386Thionyl ChlorideSolvent

Procedure

The reaction is carried out as in Example 1, starting with 4-(4-methoxyphenyl)benzo[b]thiophene-6-carboxylic acid (2.9 g) in toluene (30 cc) and thionyl chloride (2.3 cc) and triethylamine (4.3 cc) and diethylamine (1.1 cc) in anhydrous toluene (30 cc). After chromatography of the residue on silica gel using a cyclohexane:ethyl acetate (80:20 by volume) mixture as the eluent and recrystallization in isopropyl ether, N,N-diethyl-4-(4-methoxyphenyl)benzo[b]thiophene-6-carboxamide (1.12 g), m.p. 88° C., is isolated.

Workup

  1. customAfter chromatography of the residue on silica gel using a cyclohexane:ethyl acetate (80:20 by volume) mixture as the eluent and recrystallization in isopropyl ether

Sources & evidence

ORD record
ord-441ad74e90b642f6b54a288578a0df57
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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