4-[(4-Chlorophenyl)amino]-5-methylthiothiophene-2-carboxamidine hydrochloride → 4-[(4-Chlorophenyl)amino]-5-methylthiothiophene-2-carboxamidine

HRID 412979Notes

Reaction equation

HRID 412979 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:11]=[C:12]([C:17]([NH2:19])=[NH:18])[S:13][C:14]=2[S:15][CH3:16])=[CH:5][CH:4]=1.ClC1C=CC(NC2C=C(C(OC)=S)SC=2C)=CC=1.C[Al](C)C.[NH4+].[Cl-]>>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[CH:11]=[C:12]([C:17]([NH2:19])=[NH:18])[S:13][C:14]=2[S:15][CH3:16])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 185370214-[(4-Chlorophenyl)amino]-5-methylthiothiophene-2-carboxamidine hydrochlorideHCID 22243074Ammonium chloride trimethylaluminiumHCID 86583852Methyl 4-[(4-chlorophenyl)amino]-5-methylthiothiophene-2-carboxylate

Product 1

HCID 185370224-[(4-Chlorophenyl)amino]-5-methylthiothiophene-2-carboxamidineYield 100%

Procedure

4-[(4-chlorophenyl)amino]-5-methylthiothiophene-2-carboxamidine hydrochloride: Using a procedure similar to Example 154, step (b), 11.8 mg (0.037 mmol) of methyl 4-[(4-chlorophenyl)amino]-5-methylthiothiophene-2-carboxylate was allowed to react with 8 equiv (2.96 mmol) of the AlMe3/NH4Cl reagent to afford 13 mg (100%) of 4-[(4-chlorophenyl)amino]-5-methylthiothiophene-2-carboxamidine. 1H NMR (DMSO-d6, 400 MHz) δ 2.41 (s, 3H), 6.91-6.95 (m, 2H) 7.10-7.13 (m, 2H), 7.64 (s, 1H), 7.93 (s, 1H), 8.67 (bs, 2H), 9.11 (bs, 2H). Mass spectrum (ESI, m/z): Calcd. for C12H12ClN3S2, 298.02 (M+H), found 298. 1.

Sources & evidence

ORD record
ord-e2f489d7126e4d288bd74a8dc507f8d6
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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