Triethylamine → N-(3-methylpent-1-yn-3-yl)-4-amino-3-chloro-5-methoxyiminomethylbenzamide

HRID 583147

Reaction equation

[NH2:1][C:2]1[C:10]([CH:11]=[N:12][O:13][CH3:14])=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[Cl:15].C(N(CC)CC)C.CS(Cl)(=O)=O.Cl.[NH2:29][C:30]([CH3:35])([CH2:33][CH3:34])[C:31]#[CH:32]>O.O1CCCC1>[CH3:35][C:30]([NH:29][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([CH:11]=[N:12][O:13][CH3:14])[C:2]([NH2:1])=[C:3]([Cl:15])[CH:4]=1)([CH2:33][CH3:34])[C:31]#[CH:32]

Participants

Conditions

Temperature: -30 °C

Procedure

In a 100 ml, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 1.27 g (5.5 mmole) of the preceding 4-amino-3-chloro-5-methoxyiminomethylbenzoic acid, (25 ml of tetrahydrofuran and 2.31 ml (16.6 mmole) of triethylamine. The resulting well-stirred mixture was cooled to -30° C. and 0.47 ml (6.1 mmole) of methane sulfonyl chloride were added dropwise keeping the reaction temperature at -30° C. The resulting suspension was stirred at -30° C. during 30 minutes, after which 0.74 g (5.5 mmole) of 3-amino-3-methyl-1-pentyne hydrochloride were added over a 20 minute period. After the addition was completed, the reaction mixture was stirred at -30° C. for an additional 30 minutes. The reaction mixture was poured into water and extracted with methylene chloride (3×25 ml). The combined organic phases were washed sequentially with water (1×20 ml), 5% aqueous hydrochloric acid (2×20 ml), water (1×20 ml), 2% aqueous sodium hydroxide (2×20 ml) and then with water (1×20 ml) and dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, yielding 1.05 g of the expected N-(3-methylpent-1-yn-3-yl)-4-amino-3-chloro-5-methoxyiminomethylbenzamide, used in the next step without further purification.

Workup

customIn a 100 ml, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet
customat -30° C
stirringThe resulting suspension was stirred at -30° C. during 30 minutes
additionAfter the addition
stirringthe reaction mixture was stirred at -30° C. for an additional 30 minutes
extractionextracted with methylene chloride (3×25 ml)
washThe combined organic phases were washed sequentially with water (1×20 ml), 5% aqueous hydrochloric acid (2×20 ml), water (1×20 ml), 2% aqueous sodium hydroxide (2×20 ml)
dry with materialwith water (1×20 ml) and dried over anhydrous magnesium sulfate
customThe solvent was removed
customa rotary evaporator

Sources & evidence

ORD record: ord-9be8f270a6a2439792cdae4a7fd2a072
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05929098

Linked notes

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