Phenylacetyl isothiocyanate → HCID 59424501, compound

HRID 1261297Notes

Reaction equation

HRID 1261297 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[S:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[O:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[CH:8]=2)[N:4]=[CH:3]1.[C:24]1([CH2:30][C:31]([N:33]=[C:34]=[S:35])=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[S:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[O:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:34]([NH:33][C:31](=[O:32])[CH2:30][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[S:35])=[CH:19][CH:18]=3)[CH:8]=2)[N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 59424602HCID 59424602, compound

Product 1

HCID 59424501HCID 59424501, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the 226 (385 mg, ˜0.99 mmol) in THF (10 mL) was added 2-phenylacetyl isothiocyanate (263 mg, 1.49 mmol). The reaction mixture was stirred for 1 hr, transferred onto a chromatography column and eluted with EtOAc/MeOH (9:1) producing a solid material which was re-crystallized from MeCN to afford title compound 227 (74.3 mg, 15% yield) as a white solid. 1HNMR: (DMSO-d6) d(ppm): 12.39 (s, 1H), 11.73 (s, 1H), 8.43 (d, J=5.3 Hz, 1H), 7.84 (s, 1H), 7.72 (m, 3H), 7.66 (s, 1H), 7.34-7.27 (m, 7H), 6.69 (d, J=5.3 Hz, 1H), 3.82 (s, 2H), 3.72 (s, 3H). MS (m/z): 500.1 (M+1).

Workup

  1. washeluted with EtOAc/MeOH (9:1)
  2. customproducing a solid material which
  3. customwas re-crystallized from MeCN

Sources & evidence

ORD record
ord-f8ca1faea18d41c394232e8d0dd202d0
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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