Phenylacetyl isothiocyanate → HCID 59424623, compound

HRID 500857Notes

Reaction equation

HRID 500857 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:24][CH3:25])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=3)[S:17][C:10]=12.[C:26]1([CH2:32][C:33]([N:35]=[C:36]=[S:37])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([N:24]([CH3:25])[C:36]([NH:35][C:33](=[O:34])[CH2:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[S:37])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=3)[S:17][C:10]=12

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 59424428HCID 59424428, compound

Product 1

HCID 59424623HCID 59424623, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the 222 (102 mg, 2.88 mmol) in THF (3 ml) was added 2-phenylacetyl isothiocyanate (51 mg, 0.288 mmol). The reaction mixture was stirred for 1 hr, transferred onto a chromatography column and eluted with a mixture EtOAc/MeOH (19: 1) to afford title compound 223 (30 mg, 20% yield) as a white solid. 1HNMR: (DMSO-d6) δ (ppm): 10.88 (s, 1H), 8.51 (d, J=5.3 Hz, 1H), 7.91 (s, 1H), 7.41-7.18 (m, 6H), 7.04 (m, 4H), 6.5 (d, J=5.3 Hz, 1H), 4.0 (s, 3H), 3.6 (s, 2H), 3.43 (s, 3H). MS (m/z): 532.3 (M+1).

Workup

  1. washeluted with a mixture EtOAc/MeOH (19: 1)

Sources & evidence

ORD record
ord-8bd131642a12445eb6e5543125c2f59d
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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