Ethanethiol → HCID 10624314, compound

HRID 609815Notes

Reaction equation

HRID 609815 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]2[CH:14]=[C:15]([O:18]C)[CH:16]=[CH:17][C:11]=2[C:10]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:24][CH:23]=1)=[O:21].C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[S:13][C:12]2[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=2[C:10]=1[C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]2[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)=[CH:24][CH:23]=1)=[O:21]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 10791553HCID 10791553, compound

Product 1

HCID 10624314HCID 10624314, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

By the method described in Example 2, the product of Example 9 (560 mg, 1.12 mmol), ethanethiol (0.42 mL, 5.77 mmol), and aluminum chloride (1.05 g, 7.88 mmol) were stirred in anhydrous CH2Cl2 (30 mL) to provide, after chromatography (silica gel, 5-10% methznol in CH2Cl2), 257 mg (49%) of the title product as a yellow foam: 1H NMR d 1.47 (m, 2H), 1.62 (m, 4H), 2.54 (m, 4H), 2.75 (t, J=5.4 Hz, 2H), 4.10 (t, J=5.4 Hz, 2H), 4.87 (br s, 2H), 6.64 (d, J=8.1 Hz, 1H), 6.72-6.85 (m, 4H), 7.02 (m, 1H), 7.25 (m, 2H), 7.47 (d, J=8.9 Hz, 1H), 7.67 (d, J=8.6 Hz, 2H); MS (FD) m/e 473 (M+); Anal. calc'd. for C28H27NO4S: C, 71.01; H, 5.75; N, 2.96. Found: C, 71.27; H, 5.82; N, 3.19.

Workup

  1. customto provide

Sources & evidence

ORD record
ord-c55a7dd2afda48e2be4095d18eb2d794
Source dataset
uspto-grants-1999_12
Patent number
US05998442

Reaction notes

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