Methyl 3-amino-4-chloro-2-((3-hydroxypropyl)amino]benzoate → HCID 86632894, compound

HRID 1628501Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7][CH3:8])=[O:6].[N:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][C:22]=1[CH3:30])=[C:19]=[S:20]>O1CCCC1>[C:25]([C:24]1[CH:28]=[CH:29][C:21]([NH:18][C:19]([NH:1][C:2]2[C:3]([NH:13][CH2:14][CH2:15][CH2:16][OH:17])=[C:4]([CH:9]=[CH:10][C:11]=2[Cl:12])[C:5]([O:7][CH3:8])=[O:6])=[S:20])=[C:22]([CH3:30])[CH:23]=1)(=[O:26])[NH2:27]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 3-amino-4-chloro-2-[(3-hydroxypropyl)amino]benzoate (2.09 g, 8.08 mmol) and 4-isothiocyanato-3-methylbenzamide (2.33 g, 12.1 mmol) in tetrahydrofuran (20 mL) was stirred at 60° C. for 2 days. The mixture was concentrated in vacuo, and the residue was washed with ethyl acetate to give methyl 3-{[(4-carbamoyl-2-methylphenyl)carbamothioyl]amino}-4-chloro-2-[(3-hydroxypropyl)amino]benzoate as a colorless powder (2.10 g).

Workup

concentrationThe mixture was concentrated in vacuo
washthe residue was washed with ethyl acetate

Sources & evidence

ORD record: ord-aedbbca381cc48b7a143d2c49916082b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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