Ethanethiol → 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-hydroxybenzamide

HRID 1608202Notes

Reaction equation

[H-].[Na+].C(S)C.[NH2:6][C:7]1[C:29]([Cl:30])=[CH:28][C:10]([C:11]([NH:13][CH2:14][CH:15]2[O:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16]2)=[O:12])=[C:9]([O:31]C)[CH:8]=1>CN(C)C=O>[NH2:6][C:7]1[C:29]([Cl:30])=[CH:28][C:10]([C:11]([NH:13][CH2:14][CH:15]2[O:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16]2)=[O:12])=[C:9]([OH:31])[CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred suspension of 60% sodium hydride (0.52 g) in dimethylformamide (20 ml) is added under ice-coolinga solution of ethanethiol (0.81 g) in dimethylformamide (5 ml). After the mixture is stirred at 25° C. for 0.5 hour, 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-methoxybenzamide (3.4 g) is added, and the mixture is stirred at 100° C. for 1 hour. After cooling, the reaction mixture is evaporated under reduced pressure. The residue is diluted with water, washed with chloroform, and neutralized with 10% hydrochloric acid. The precipiate is collected, washed with water, and recrystallized from isopropyl alcohol to give the monohydrate of the title compound (2.3 g), mp 153°-155° C.

Workup

stirringthe mixture is stirred at 100° C. for 1 hour
temperatureAfter cooling
customthe reaction mixture is evaporated under reduced pressure
additionThe residue is diluted with water
washwashed with chloroform
customThe precipiate is collected
washwashed with water
customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record: ord-fcafa61a702442e7bdd3a3bf7b8ff2a4
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870074

Reaction notes

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