Hydrochloric Acid → 2,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]phenyl thiocyanate

HRID 326790Notes

Reaction equation

HRID 326790 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](Cl)=[O:10].C(=O)([O-])[O-].[Ca+2].[NH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([S:25][C:26]#[N:27])=[C:20]([CH3:28])[CH:19]=1.Cl>C1COCC1.O>[CH3:24][C:22]1[CH:23]=[C:18]([NH:17][C:9](=[O:10])[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH:19]=[C:20]([CH3:28])[C:21]=1[S:25][C:26]#[N:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 2760632o-Tolyl-acetyl chlorideHCID 150159523,5-Dimethyl-4-thiocyanatoaniline

Product 1

HCID 150159532,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]phenyl thiocyanateYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Methylphenyl)acetyl chloride (9.9 g, 58.8 mM) was added to a stirred suspension of calcium carbonate (7.87 g, 78.7 mM) and 4-amino-2,6-dimethylphenyl thiocyanate (7 g, 39.3 mM) in dry THF (150 mL). The mixture was stirred for 1 hour. Water (1000 mL) was added. The mixture was acidified to pH4 with 2M HCl and extracted with ethyl acetate. The combined extracts were washed with water, then with saturated sodium chloride solution and dried (MgSO4). The solvent was removed by evaporation. The pale green solid obtained was triturated with ether to give 2,6-dimethyl-4-[2-(2-methylphenyl)acetamido]phenyl thiocyanate (B), as a cream coloured solid in 83% yield; NMR (CDCl3, 200 MHz): 2.47(s, 3H), 2.49(s, 6H), 3.69(s, 2H), 7.14-7.17(m, 4H), 7.55(s, 2H), 10.27(s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialwith saturated sodium chloride solution and dried (MgSO4)
  4. customThe solvent was removed by evaporation
  5. customThe pale green solid obtained
  6. customwas triturated with ether

Sources & evidence

ORD record
ord-7385763bd36c4a3a8e02833283ca52bf
Source dataset
uspto-grants-1993_12
Patent number
US05270342

Reaction notes

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