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

HRID 381210Notes

Reaction equation

HRID 381210 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-0fb57e503c5d4167bde0f2a0c943c405
Source dataset
uspto-grants-2001_10
Patent number
US06306570B1

Reaction notes

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