Anthranilic Acid → HCID 882553, compound

HRID 1599822Notes

Reaction equation

HRID 1599822 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11]1([S:17][CH2:18][C:19](Cl)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.O>[OH-].[Na+]>[C:11]1([S:17][CH2:18][C:19]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 4063350(Phenylthio)acetyl chloride

Product 1

HCID 882553HCID 882553, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 6.3 g of anthranilic acid in aqueous NaOH (4 g of NaOH in 40 mL of water) which was cooled using an ice-bath was added 8.6 g (0.046 mol) of phenylmercaptoacetylchloride from Example 46. The reaction mixture was stirred for 1 h. The reaction mixture was neutralized with 5% HCl, water (50 mL) was added, and then the mixture was extracted with EtOAc (3×100 mL). The EtOAc solution was dried, filtered, and then concentrated to give after drying under high vacuum, 7.0 g (53%) of the title compound, mp 166°-167° C. (lit. 164°-166° C. (Gorlitzer, K.; Weber, J. Arch. Pharm (Weinheim) 1980, 314, 76)); 1H NMR (DMSO-d6) δ11.82 (s, 1H, COOH), 8.51 (s, 1H, J=8.4),7.96 (dd, 1H, J=1.2, J=8), 7.58 (t, 1H, J=8), 7.38 (d,1H, J=7.2), 7.13 (m, 5H), 4.01 (s, 2H); 13C NMR (DMSO-d6) δ169.17, 167.42, 140.31, 135.00, 134.07, 133.72, 131.12, 129.18, 128.07, 126.33, 123.01, 119.77, 116.58, 116.31, 114.54; MS (EI, m/z) 287 (M+). HRMS (EI) calcd for C15H13N2 O3S 287.0616, found 287.0617.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EtOAc (3×100 mL)
  3. dry with materialThe EtOAc solution was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give
  7. dry with materialafter drying under high vacuum, 7.0 g (53%) of the title compound, mp 166°-167° C. (lit. 164°-166° C. (Gorlitzer, K.; Weber, J. Arch. Pharm (Weinheim) 1980, 314, 76))

Sources & evidence

ORD record
ord-2fbb2250e1f941379babf548c22e4cdb
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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