Phenyl isocyanate → HCID 11574533, compound

HRID 746370Notes

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][C:5]2[CH:9]=[C:10]3[C:15](=[CH:16][C:4]=2[S:3]1(=[O:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]3.[H-].[Na+].[H][H].[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]([C:30]([NH:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:31])[C:5]2[CH:9]=[C:10]3[C:15](=[CH:16][C:4]=2[S:3]1(=[O:17])=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11]3

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 5 g (19 mmol) 3,4,6,7,8,9-hexahydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine 1,1-dioxide in 100 mL tetrahydrofuran was added to a suspension of 0.7 g (29 mmol) sodium hydride in 50 mL tetrahydrofuran at −5° C. under N2. After termination of the hydrogen formation 5.7 g (48 mmol) phenylisocyanate dissolved in 50 mL tetrahydrofuran were added at −5° C. After stirring at room temperature (approx. 20° C.) the resulting mixture was quenched with ice/water and by addition of dilute HCl and then extracted with CH2Cl2 (2 times). The combined CH2Cl2 extracts were washed, dried and concentrated to give 6 g crude product. This material was recrystallized from ethanol to give 3.6 g 3,4,6,7,8,9-hexahydro-2-methyl-3-oxo-2H-naphtho[2,3-e]-1,2-thiazine-4-carboxanilide 1,1-dioxide.

Workup

additionwere added at −5° C
customwas quenched with ice/water and by addition of dilute HCl
extractionextracted with CH2Cl2 (2 times)
washThe combined CH2Cl2 extracts were washed
customdried
concentrationconcentrated
customto give 6 g crude product
customThis material was recrystallized from ethanol

Sources & evidence

ORD record: ord-7fd30dab31e94c00abcdb11ccdd1a61a
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393843B2

Reaction notes

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