1-Methyl-1-acetyl-4-{4-(N-methyl-N-carboethoxymethylamino)phenyl}-3-thiosemicarbazide → HCID 178472693, compound

HRID 1005273Notes

Reaction equation

HRID 1005273 reaction equation
[CH3:1][N:2]([C:21](=O)[CH3:22])[NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)=[S:5]>C(O)CCC>[CH3:1][N+:2]1[N:3]=[C:4]([S-:5])[N:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]([CH3:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=2)[C:21]=1[CH3:22]

Participants

3

Reactant 1

HCID 120388611-Methyl-1-acetyl-4-{4-(N-methyl-N-carboethoxymethylamino)phenyl}-3-thiosemicarbazide

Product 1

HCID 178472693HCID 178472693, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2.03 g (6.06 mmol) of 1-methyl-1-acetyl-4-{4-(N-methyl-N-carboethoxymethylamino)phenyl}-3-thiosemicarbazide in 50 ml of butanol was heated at reflux until tlc showed no starting material (Rf 0.3,EtOAc,5 hr). Solvent was distilled and the residue crystallized with ethyl acetate. The solid (1.2 g) was recrystallized from 25 ml of water to give 0.978 g (3.05 mmol,50%), mp 211°. Anal. C15H20N4O2S (320): Calcd.: C,56.23; H,6.29; N,17.49; S,10.01. Found: C,56.30; H,6.20; N,17.93; S,9.61. MS(FD) 320. 1H NMR (DMSO-d6):δ 7.08,d,2H,ArH; 6.71,d,2H,ArH; 4.23,s,2H, CH3--N; 4.08,q,2h,CH2--O; 3.68,s,3H,CH3--N+ ; 3.29,s,3H,CH3--N; 2.23,s,3H,CH3--C=; 1.16,t,3H,CH3--C.

Workup

  1. temperatureat reflux until tlc
  2. distillationSolvent was distilled
  3. customthe residue crystallized with ethyl acetate
  4. customThe solid (1.2 g) was recrystallized from 25 ml of water
  5. customto give 0.978 g (3.05 mmol,50%), mp 211°

Sources & evidence

ORD record
ord-0572ba28350349f4aff0d28f60590280
Source dataset
uspto-grants-2000_04
Patent number
US06054260

Reaction notes

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