Diethylamine → HCID 14054340, compound

HRID 1382862Notes

Reaction equation

HRID 1382862 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[CH:15]=[CH:14][S:13][C:12]=3[CH:11]=[C:10]([C:17]([OH:19])=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH2:20]([N:22](CC)[CH2:23][CH3:24])[CH3:21].C(NCC)C.C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1.S(Cl)(Cl)=O>[CH2:20]([N:22]([CH2:23][CH3:24])[C:17]([C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:16]2[CH:15]=[CH:14][S:13][C:12]=2[CH:11]=1)=[O:19])[CH3:21]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 13637983HCID 13637983, compoundHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 14054340HCID 14054340, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

The reaction is carried out as in Example 1, starting with 4-(4-chlorophenyl)benzo[b]thiophene-6-carboxylic acid (4.67 g) in toluene (45 cc) and thionyl chloride (3.6 cc) and then triethylamine (6.9 cc) and diethylamine (1.7 cc) in toluene (45 cc). After chromatography of the residue using a cyclohexane:ethyl acetate (90:10 by volume) mixture as the eluent, a residue is obtained, which is stirred for 2 hours in 40°-60° petroleum spirit. After filtering and drying, N,N-diethyl-4-(4-chlorophenyl)benzo[b]thiophene-6-carboxamide (1.07 g), m.p. 135° C., is obtained.

Workup

  1. customa residue is obtained
  2. filtrationAfter filtering
  3. customdrying

Sources & evidence

ORD record
ord-d64db60bf82f4973b80e9e726e39336d
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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