Thiourea → 2-Amidinothiomethyl-5-(dimethylamino)methyl-4-methylthiophene dihydrochloride

HRID 1650199Notes

Reaction equation

HRID 1650199 reaction equation
[ClH:1].C(O)(C)C.[NH2:6][C:7]([NH2:9])=[S:8].[CH3:10][N:11]([CH2:13][C:14]1[S:18][C:17]([CH2:19]O)=[CH:16][C:15]=1[CH3:21])[CH3:12]>>[ClH:1].[ClH:1].[C:7]([S:8][CH2:19][C:17]1[S:18][C:14]([CH2:13][N:11]([CH3:12])[CH3:10])=[C:15]([CH3:21])[CH:16]=1)(=[NH:9])[NH2:6]

Participants

4

Reactant 3

HCID 2723790ThioureaHCID 129265355-(Dimethylamino)methyl-4-methyl-2-thenyl alcoholHCID 21912024Isopropanol hydrochloride

Product 1

HCID 138252712-Amidinothiomethyl-5-(dimethylamino)methyl-4-methylthiophene dihydrochlorideYield 82%

Procedure

In 35 ml of 21% (by weight) hydrochloric acid-isopropanol solution was suspended 2.1 g of thiourea, and 5 g of 5-(dimethylamino)methyl-4-methyl-2-thenyl alcohol was added thereto, after which the resulting mixture was subjected to reaction under reflux for 15 hours. After the mixture was allowed to stand at room temperature, the crystals deposited were collected by filtration to obtain 7 g (yield 82%) of 2-amidinothiomethyl-5-(dimethylamino)methyl-4-methylthiophene dihydrochloride having a melting point of 212°-214° C. (decomp.). NMR (d6 -DMSO) δ values: 2.31 (3H, s, --CH3), 2.82 (6H, s, --CH3 ×2), 4.58 (2H, s, >CH2), 5.04 (2H, s, >CH2), 7.16 (1H, s, thiophene ring H), 9.76 (4H, bs, ##STR224## 11.01 (1H, bs, HCl)

Workup

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction
  3. temperatureunder reflux for 15 hours
  4. customto stand at room temperature
  5. filtrationthe crystals deposited were collected by filtration

Sources & evidence

ORD record
ord-d5a93c83e6784f53ac559aa06bf7d583
Source dataset
uspto-grants-1990_05
Patent number
US04923882

Reaction notes

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