Toluene → HCID 9901114, compound

HRID 895333Notes

Reaction equation

HRID 895333 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].ClC1C=[CH:16][S:15][C:14]=1C(OCCCCCCCC)=O.[C:29]1([CH3:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:14]([S:15][C:16]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=2[N:1]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:29][CH3:35]

Participants

6

Reactant 3

HCID 1140TolueneHCID 762552-Amino-5-methylbenzoic acidHCID 69133002HCID 69133002, compound

Product 1

HCID 9901114HCID 9901114, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-methylbenzoic acid (1.51 g, 10 mmol) was dissolved in pyridine (10 ml), and to this was added the crude octyl chlorothiolformate (28 mmol, assuming 100% from the first step) as a solution in toluene. After 2 h, the reaction was diluted with ethyl acetate and washed three times with 1M aqueous HCl, then saturated aqueous sodium bicarbonate, water and brine. The organic phase was dried (MgSO4) and concentrated in vacuo. Crystallisation from hexane gave the title compound (155 mg, 5%): δH (400 MHz, CDCl3) 0.91 (3H, t, J 7.0, Me), 1.30-1.34 (8H, m, 4×CH2), 1.44-1.50 (2H, m, SCH2CH2CH2), 1.79 (2H, qn, J 7.4, SCH2CH2), 2.46 (3H, s, ArMe), 3.16 (2H, t, J 7.3, SCH2), 7.38 (1H, d, J 8.2, ArH), 7.58 (1H, dd, J 8.2, 1.8, ArH), 7.93 (1H, s, ArH); m/z (ES+) 306 (MH+).

Workup

  1. washwashed three times with 1M aqueous HCl
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customCrystallisation from hexane

Sources & evidence

ORD record
ord-0af1b8572b6c44cda9de10a20e48541e
Source dataset
uspto-grants-2005_07
Patent number
US06916808B2

Reaction notes

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