Triethylamine → HCID 14054312, compound

HRID 1382855Notes

Reaction equation

HRID 1382855 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.C(N(CC)CC)C.[CH3:26][CH:27]([NH2:30])[CH2:28][CH3:29].C1CCCCC1.C(OCC)(=O)C>C1(C)C=CC=CC=1.S(Cl)(Cl)=O>[CH3:26][CH:27]([NH:30][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])[CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24874Sec-ButylamineHCID 14054310HCID 14054310, compoundHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 14054312HCID 14054312, 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 (2.6 cc) and then adding triethylamine (9.94 cc) and 2-butanamine (1.2 cc) in toluene (30 cc). After chromatography of the residue on silica gel using a cyclohexane:ethyl acetate (50:50 by volume) mixture as the eluent, N-(1-methylpropyl)-7-phenylbenzo[b]thiophene-5-carboxamide (2.35 g), m.p. 195° C., is obtained.

Sources & evidence

ORD record
ord-f8693a6c8a4f4972a6b9c59999a15cd7
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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