Ethanethiol → HCID 21462366, compound

HRID 1940488Notes

Reaction equation

HRID 1940488 reaction equation
B(F)(F)F.CCOCC.[CH2:10](S)[CH3:11].[F:13][C:14]1[C:27]([NH:28][C:29]([CH:31]2[CH2:35][CH2:34]C[N:32]2C(OCC2C=CC=CC=2)=O)=[O:30])=[CH:26][C:17]2[N:18]([CH2:23][C:24]#[CH:25])[C:19](=[O:22])[CH2:20][O:21][C:16]=2[CH:15]=1.[OH-].[Na+].O>C(Cl)Cl.O>[F:13][C:14]1[C:27]([NH:28][C:29]([CH:31]2[NH:32][CH2:10][CH:11]3[CH:35]2[CH2:34]3)=[O:30])=[CH:26][C:17]2[N:18]([CH2:23][C:24]#[CH:25])[C:19](=[O:22])[CH2:20][O:21][C:16]=2[CH:15]=1

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 21462369HCID 21462369, compoundHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 21462366HCID 21462366, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of boron trifluoride etherate (1.57 gm, 10.8 mmol) and ethanethiol (2.31 mL, 1.94 gm, 32.32 mmol) under N2, at room temperature was added dropwise a solution of the compound of Step F, Example 3, (500.0 mg) in CH2Cl2 (1 mL). The resultant clear solution was stirred at room temperature for 48 hours and the reaction was scrubbed with a bleach/50% NaOH/H2O-20%. 30 mL of water was added dropwise at room temperature followed by CH2Cl2 (30 mL). The aqueous layer was separated and basified to pH 10 using 50% NaOH. Additional 30 mL of CH2Cl2 was added and the organic layer was separated, dried (MgSO4) and evaporated to dryness to give the title compound of Step G as a white solid (200 mg), 57%; m.p. 196°-198° C.; IR (nujol, cm-1): 1676.0 (C=O), 3357.7 and 3301.7 (NH); 1H NMR δ: 0.08-0.09 (m,1H), 0.71-0.77 (m,1H), 1.41-1.43 (m,1H), 2.01-2.08 (m,1H), 2.11-2.17 (broad s, 1H), 2.31-2.32 (m,1H), 3.02 (s,2H), 3.72 (s,1H), 4.61 (s,2H), 4.75-4.81 (dd,2H), 6.79-6.81 (d,1H), 8.44-8.46 (d,1H), 9.85 (broad s,1H).

Workup

  1. customThe aqueous layer was separated
  2. additionAdditional 30 mL of CH2Cl2 was added
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-a1c6f108f85044f6b458c1137f23ab6a
Source dataset
uspto-grants-1997_12
Patent number
US05700761

Reaction notes

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