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

HRID 1608202
Notes
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Reaction equation

HRID 1608202 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 1972374-amino-N-((4-benzyl-2-morpholinyl)methyl)-5-chloro-2-methoxybenzamide

Product 1

HCID 148819784-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-hydroxybenzamideYield 70.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent
2×

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

  1. stirringthe mixture is stirred at 100° C. for 1 hour
  2. temperatureAfter cooling
  3. customthe reaction mixture is evaporated under reduced pressure
  4. additionThe residue is diluted with water
  5. washwashed with chloroform
  6. customThe precipiate is collected
  7. washwashed with water
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes