Thiophenol → HCID 51892979, compound

HRID 1160736Notes

Reaction equation

HRID 1160736 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][N:14]1[C:18]([S:19]([C:22]2[CH:27]=[CH:26][C:25](C)=[CH:24][CH:23]=2)(=O)=O)=[N:17][N:16]=[N:15]1)(OC(C)(C)C)=O.C1C=CC(S)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:22]1([S:19][C:18]2[N:14]([CH2:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)[N:15]=[N:16][N:17]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 57332418HCID 57332418, compound

Product 1

HCID 51892979HCID 51892979, compoundYield 135.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of 2 (6.0 g, 14.7 mmol), phenylthiol (6.5 g, 58.8 mmol) and K2CO3 (4.5 g, 41.1 mmol) in CH3CN (74 ml) was stirred for 2 days at room temperature. The reaction mixture was filtered through a pad of Celite and then concentrated in vacuo. The crude was purified by silica gel column with (Hexane:EtOAc=1:1) as an eluant to give 3 (5.2 g, 97%) as an colorless oil. [α]D −29.2 (c 1.34, CHCl3). 1H NMR (400 MHz, CD3OD, −20° C., rotamers 1:1): δ 1.30 & 1.42 (s, 9H), 1.73 & 2.01 (m, 4H) 3.40 & 3.45 (m, 13.2 Hz, 2H), 4.23 & 4.25 (m, 1H), 4.38 & 4.58 (m, 2H), 7.42 & 7.46 (m, 3H) 7.56 & 7.60 (m, 2H); 13C NMR (CDCl3, 75 MHz): δ 21.2, 23.6, 28.5, 46.5, 49.7, 50.4, 56.7, 60.5, 80.7, 128.1, 129.9, 133.1, 153.5, 154.9; IR (film): 2975, 1693, 1391, 1167, 688 cm−1; MS:(ESI) [M+1]+361.2

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated in vacuo
  3. customThe crude was purified by silica gel column with (Hexane:EtOAc=1:1) as an eluant

Sources & evidence

ORD record
ord-63a4497915a84ad7aef8ab8c79b14047
Source dataset
uspto-grants-2010_10
Patent number
US07816538B2

Reaction notes

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