Hydrochloric Acid → 2-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic acid

HRID 992590Notes

Reaction equation

HRID 992590 reaction equation
Cl.[NH2:2][CH2:3][C:4]([CH3:7])([SH:6])[CH3:5].C(N(CC)CC)C.[CH:15]1[C:25]2[C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[C:22](=[O:30])[O:21][C:20](=[O:31])[C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl>C(Cl)Cl>[CH3:5][C:4]([SH:6])([CH3:7])[CH2:3][NH:2][C:22]([C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[C:25]1[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=1[C:20]([OH:31])=[O:21])=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 72794Diphenic anhydrideHCID 130491041-Amino-2-methyl-2-propanethiol hydrochloride

Product 1

HCID 184127982-{2-[N-(2-methyl-2-sulfanylpropyl)carbamoyl]phenyl}benzoic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled suspension of 1-amino-2-methyl-2-propanethiol hydrochloride (1.08 g, 7.62 mmol) in methylene chloride (20 mL) was added triethylamine (1.2 mL, 8.61 mmol) followed by dibenzo[c,e]oxepin-5,7-dione (1.68 g, 7.42 mmol). After stirring at room temperature for 1 h, cold 2 N HCl (50 mL) was added. After separation, the aqueous layer was extracted with dichloromethane (2×15 mL). The combined organic layers were washed with brine and dried under sodium sulfate. The solvent was removed and the resulting residue was triturated with hexane to give the title compound as white solid (2.44 g, 98.9%). mp 150-153° C.; 1H NMR (CDCl3, 300 MHz): δ1.03 (s, 3H), 1.12 (s, 3H), 1.36 (s, 1H), 3.15 (dd, J=13.7 and 5.7 Hz, 1H), 3.38 (dd, J=13.7 and 6.9 Hz, 1H), 6.92 (t, J=6.1 Hz, 1H), 7.09-7.17 (m 2H), 7.38-7.48 (m, 4H), 7.57-7.61 (m, 1H), 7.80-7.83 (m, 1H); 13C NMR (CDCl3, 75 MHz,): δ29.36, 29.75, 44.66, 53.01, 127.28, 127.96, 128.04, 129.38, 129.93, 130.06, 130.20, 131.19, 132.02, 134.69, 138.90, 140.11, 170.99, 171.24; LCMS (m/e): 330 (M+1).

Workup

  1. customAfter separation
  2. extractionthe aqueous layer was extracted with dichloromethane (2×15 mL)
  3. washThe combined organic layers were washed with brine
  4. customdried under sodium sulfate
  5. customThe solvent was removed
  6. customthe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-31a34c28163c468a9ba5ea74de995ad3
Source dataset
uspto-grants-2002_10
Patent number
US06469065B1

Reaction notes

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