Triethylamine → HCID 23348602, compound

HRID 1855779Notes

Reaction equation

[NH2:1][CH2:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].[C:9](Cl)(Cl)=[S:10].C(N(CC)CC)C.[NH2:20][CH2:21][N:22]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=[O:29]>C(Cl)Cl>[O:29]=[C:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:22]1[CH2:21][NH:20][C:9]([NH:1][CH2:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])=[S:10]

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of 6.27 g (0.055 mole) of 1-aminomethyl-2-pyrrolidinone in 50 ml of methylene chloride is added slowly and with vigorous stirring to a solution of 3.8 ml (0.05 mole) of thiophosgene and 10.1 g (0.1 mole) of triethylamine in 50 ml of methylene chloride kept at -70° C. After the addition, the reaction mixture is allowed to return to ambient temperature and 7.8 g (0.005 mole) of 1-aminomethyl-hexahydro-2H-azepin-2-one are added slowly. Stirring is continued for 15 minutes and the reaction mixture is then cooled to -50° C. in order to precipitate the triethylamine hydrochloride. It is filtered and the filtrate is evaporated to dryness. The residue obtained is purified by chromatograhy on silica (eluent: chloroform). 5.9 g of 1-[(hexahydro-2-oxo-1H-azepin-1-yl)methyl]-3-[(2-oxo-pyrrolidino)methyl]-2-thiourea are obtained. Yield: 39% of theory; M.P. 147°-148° C.

Workup

customkept at -70° C
additionAfter the addition
customto return to ambient temperature
customto precipitate the triethylamine hydrochloride
filtrationIt is filtered
customthe filtrate is evaporated to dryness
customThe residue obtained
customis purified by chromatograhy on silica (eluent: chloroform)

Sources & evidence

ORD record: ord-4ad4f32775fe4ce5814c397056c61baa
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04216221

Reaction notes

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