Hydrochloric Acid → HCID 178425897, compound

HRID 2306664Notes

Reaction equation

HRID 2306664 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].Cl.[N:13]([O-])=O.[Na+].[C:17]([SH:21])([CH3:20])([CH3:19])[CH3:18]>O.CC(C)=O>[C:17]([S:21]/[N:13]=[N:1]/[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6387tert-Butyl mercaptanHCID 755683-Amino-4-methylbenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 178425897HCID 178425897, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 3-amino-4-methylbenzoic acid (5.0 g, 33 mmol) in a mixture of water (50 mL) and concentrated hydrochloric acid (15 mL) in an acetone-crushed ice bath is added a solution of sodium nitrite in water (12 mL) dropwise. The solution is stirred for 10 min, followed by the addition of tert-butyl mercaptan (1.8 mL, 16 mmol). The mixture is stirred for 1 h. The solid precipitate is filtered, washed with water and dried in vacuo to obtain 3.85 g (95%) of 3-[(E)-(tert-butylthio)diazenyl]-4-methylbenzoic acid as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ 13.2, 7.8, 7.5, 7.3, 2.1, 1.6.

Workup

  1. customcrushed ice bath
  2. stirringThe mixture is stirred for 1 h
  3. filtrationThe solid precipitate is filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-05999e604e114928b64a6e882871a414
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

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