2-Thiophenecarboxylic acid → HCID 13769178, compound

HRID 2232522Notes

Reaction equation

HRID 2232522 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](O)=O.S(Cl)(Cl)=O.[CH2:13]([N:15]([CH2:29][CH3:30])[C:16](=[O:28])[CH2:17][CH2:18][C:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26])[CH3:14].C([O-])(=O)C.[NH4+:35]>C(O)(=O)C.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:13]([N:15]([CH2:29][CH3:30])[C:16](=[O:28])[CH2:17][CH2:18][C:19]1[C:20]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:26]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[N:35]=1)[CH3:14]

Participants

8

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 24386Thionyl ChlorideHCID 517165Ammonium AcetateHCID 21283598HCID 21283598, compound

Product 1

HCID 13769178HCID 13769178, compoundYield 54.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

The procedure is as in Example 28, starting with 2-thienoic acid (1.15 g) and thionyl chloride (10 cc), then triethylamine (1.9 cc), N,N-diethyl-3-(2-aminobenzoyl)propanamide (1.11 g) and chloroform (20 cc), and finally ammonium acetate (5 g) and acetic acid (5 cc). After chromatography on silica gel with a cyclohexane/ethyl acetate (1:1 by volume) mixture as eluant and crystallization in isopropyl ether, N,N-diethyl-2-thienyl-4-quinazolinepropanamide (0.83 g), m.p. 106° C., is obtained.

Workup

  1. customAfter chromatography on silica gel with a cyclohexane/ethyl acetate (1:1 by volume) mixture as eluant and crystallization in isopropyl ether

Sources & evidence

ORD record
ord-df09a562eb0746d0bc2182a5c015539a
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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