Ethanethiol → HCID 69984381, compound

HRID 1602378Notes

Reaction equation

HRID 1602378 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][C:22]4[S:26][CH:25]=[N:24][C:23]=4[CH3:27])=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:28]3[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=3)[S:8][C:7]=2[CH:36]=1.[Al+3].[Cl-].[Cl-].[Cl-].CCS>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][C:22]4[S:26][CH:25]=[N:24][C:23]=4[CH3:27])=[CH:15][CH:14]=3)=[O:12])=[C:9]([C:28]3[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=3)[S:8][C:7]=2[CH:36]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 19611630HCID 19611630, compound

Product 1

HCID 69984381HCID 69984381, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of a compound of Example 11 (0.27 g, 0.52 mmol), AlCl3 (0.42 g, 3.12 mmol) and EtSH (0.19 mL, 2.6 mmol) in CH2Cl2 (10 mL) at room temp. for 0.5 h. according to the procedure described in Example 3 provided a 95% of the desired product as a yellow solid: 1H-NMR (300 MHz, CDCl3) δ9.91 (s, 1H), 9.71 (s, 1H), 8.82 (s, 1H), 7.67 (d, J=8.7 Hz, 2H), 7.35 (d, J=2.3 Hz, 1H), 7.26 (d, J=8.8 Hz, 1H), 7.18 (d, J=8.9 Hz, 2H), 6.93 (d, J=8.7 Hz, 2H), 6.86 (dd, J=8.9, 2.3 Hz, 1H), 6.66 (d, J=8.8 hz, 2H), 4.19 (t, J=3.3 Hz, 2H), 3.20 (t, J=3.6 Hz, 2H), 2.32 (s, 3H); IR (thin film) 3299, 1700, 1635 cm-1; MS (FD) 488 (M+) Anal. calcd. for C25H21O4NS2 ; calc'd/found C(66.51/66.88), H (4.34/4.49), N (2.88/2.95).

Sources & evidence

ORD record
ord-1de52b4d41724a34a9d69641d97af994
Source dataset
uspto-grants-1999_11
Patent number
US05981570

Reaction notes

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