2-Aminothiophenol → HCID 11232153, compound

HRID 636847Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Cs+].[Cs+].N[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[SH:35].C[N:37]1C(=O)CCC1>>[NH2:37][C:33]1[CH:32]=[CH:31][C:30]([S:35][C:2]2[CH:3]=[C:4]([C:8]3([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=2)=[CH:29][CH:34]=1

Participants

Reactant 5

HCID 87132-Aminothiophenol2×

HCID 10340Sodium Carbonate

HCID 10796Cesium carbonate

HCID 13387N-methyl-2-pyrrolidone

HCID 114597874-(3-bromophenyl)oxane-4-carbonitrile

Product 1

HCID 11232153HCID 11232153, compoundYield 86%

Procedure

4-(3-Bromo-phenyl)-tetrahydro-pyran-4-carbonitrile (133.4 g), Na2CO3 (363.6 g), Cs2CO3 (223.1 g) and aminothiophenol (62.8 g) were heated in N-methyl pyrrolidinone (2.3 L) at 130° C. for 24 hours. More aminothiophenol (35.6 g) was added and heating was continued for another 8 hours. The mixture was cooled to room temperature, poured onto icewater (6.8 L) and filtered off. The product was suspended in water (2.5 L) filtered again and washed with water (1.5 L). The product was then slurried in EtOH (0.5 L), filtered off and dried at 40° C./20 mbar to yield 4-[3-(4-Amino-phenyl sulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile (134.3 g, 86%).

Workup

temperatureheating
additionpoured onto icewater (6.8 L)
filtrationfiltered off
filtrationfiltered again
washwashed with water (1.5 L)
filtrationfiltered off
customdried at 40° C./20 mbar

Sources & evidence

ORD record: ord-951c1cd45cd44310925d753f61adbed4
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06194585B1

Reaction notes

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