Diethyl Ether → 1-(3-Benzoyl-thioureido)-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1261917Notes

Reaction equation

HRID 1261917 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)=[O:5])[CH3:2].[C:12]([N:20]=[C:21]=[S:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOCC>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH:11][C:21]([NH:20][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[S:22])[CH:8]=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 68284Benzoyl isothiocyanateHCID 45082088Ethyl 1-amino-1H-pyrrole-2-carboxylate

Product 1

HCID 866616611-(3-Benzoyl-thioureido)-1H-pyrrole-2-carboxylic acid ethyl esterYield 50.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Amino-1H-pyrrole-2-carboxylic acid ethyl ester (53.0 g, 0.344 mol) was dissolved in Tetrahydrofuran (2000 mL). Benzoyl isothiocyanate (56.1 g, 0.344 mol) was added and the reaction was allowed to stir overnight. The reaction mixture was reduced and 55.47 grams of 1-(3-Benzoyl-thioureido)-1H-pyrrole-2-carboxylic acid ethyl ester was isolated as a white solid via trituration with ether. (M+Na)=339.98. 1H NMR (400 MHz, DMSO, d6) δ 12.91 (s, 1H), 11.94 (s, 1H), 7.98 (d, 1H, J=7.32 Hz), 7.68 (t, 1H, J=7.52 Hz), 7.56 (t, 2H, J=7.64 Hz), 7.16 (m, 1H), 6.89 (m, 1H), 6.19 (m, 1H), 4.14 (q, 2H, J=7.12 Hz), 1.18 (d, 3H, J=14.17 Hz).

Sources & evidence

ORD record
ord-7357243a743d436aa88f703e805b65d3
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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