Hydrochloric Acid → HCID 178425897, compound

HRID 14162

Reaction equation

HRID 14162 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([O-])(=O)C.[Na+].[CH3:22][C:23]([SH:26])([CH3:25])[CH3:24]>O>[C:23]([S:26]/[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])([CH3:25])([CH3:24])[CH3:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6387tert-Butyl mercaptanHCID 755683-Amino-4-methylbenzoic acidHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178425897HCID 178425897, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 3-amino-4-methyl benzoic acid (5.0 g) in water (50 mL) was added concentrated hydrochloric acid (15 mL). The mixture was chilled to 0° C. in an ice/acetone bath. Sodium nitrite (2.28 g) was dissolved in water (10 mL) and slowly added to the mixture at 0° C. The pH was adjusted to 6 with saturated sodium acetate and 2-methyl-2-propanethiol (1.8 mL) was added. The mixture was stirred for 1 h and the resulting solids were collected by filtration, washed with water and dried under reduced pressure to give 5.7 g of the title compound: 1H NMR (CDCl3) δ 1.61, 2.20, 7.38, 7.55, 9.67.

Workup

  1. additionslowly added to the mixture at 0° C
  2. additionwas added
  3. filtrationthe resulting solids were collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-d460acee005d487d96d6209089279d3e
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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