Phosgene → 3-Thiophenecarboxylic acid, 4-(isocyanatosulfonyl)-5-methyl-, methyl ester

HRID 2243447Notes

Reaction equation

HRID 2243447 reaction equation
[NH2:1][S:2]([C:5]1[C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][S:8][C:9]=1[CH3:10])(=[O:4])=[O:3].C(N=[C:21]=[O:22])CCCC.C(Cl)(Cl)=O>>[N:1]([S:2]([C:5]1[C:6]([C:11]([O:13][CH3:14])=[O:12])=[CH:7][S:8][C:9]=1[CH3:10])(=[O:4])=[O:3])=[C:21]=[O:22]

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 206036Pentane, 1-isocyanato-HCID 11299311Methyl 5-methyl-4-sulfamoylthiophene-3-carboxylate

Product 1

HCID 579578313-Thiophenecarboxylic acid, 4-(isocyanatosulfonyl)-5-methyl-, methyl ester

Procedure

Under the conditions specified above, 23.5 g of methyl 4-(aminosulfonyl)-5-methylthiophene -3-carboxylate (1) were reacted with 11.3 g of pentyl isocyanate (100 mmol) in the presence of phosgene to give methyl 4-(isocyanatosulfonyl)-5-methylthiophene-3-carboxylate (2). 22 g of this isocyanate (83% of theory, content: 99%, b.p.: 120° C., 0.4 mbar) were likewise obtained. The identification and the determination of content were conducted by means of derivatization with methanol to the corresponding carbamate (1H NMR (400 MHz, d6DMSO): 2.72 (s), 3.61 (s), 3.79 (s), 8.00 (s), 11.96 (s)).

Sources & evidence

ORD record
ord-449e611dedbb4ea8bb033d6d7934e1d4
Source dataset
uspto-grants-2010_03
Patent number
US07674917B2

Reaction notes

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