Acetic acid, 1-methylhydrazide → 1-Methyl-1-acetyl-4-{4-(N-methyl-N-carboethoxymethylamino)phenyl}-3-thiosemicarbazide

HRID 381209Notes

Reaction equation

HRID 381209 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[S:17])=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:18][N:19]([C:21](=[O:23])[CH3:22])[NH2:20].C(O)(C)C.CCOCC>CCOCC>[CH3:18][N:19]([C:21](=[O:23])[CH3:22])[NH:20][C:16]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([N:2]([CH3:1])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:14][CH:13]=1)=[S:17]

Participants

5

Reactant 3

HCID 19051Acetic acid, 1-methylhydrazideHCID 12038855Ethyl N-methyl-N-(4-isothiocyanatophenyl)glycinateHCID 22147583Diethyl ether 2-propanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.25 g (5.0 mmol) of ethyl N-methyl-N-(4-isothiocyanatophenyl)glycinate and 0.44 g (5.0 mmol) of 1-methyl-1-acetylhydrazine in 40 ml of 1/1 isoproply alcohol/ether was left uncovered so the ether could evaporate over a 24 hr period. The product was collected and washed with isopropyl alcohol to give 1.32 g (3.9 mmol, 78%), mp 162° dec. Anal. C15H22N4O3S (338): Calcd.: C,53.24; H,6.55; N,16.56; S,9.48. Found: C,53.12; H, 6.45; N,17.05; S,8.90. MS(FD) m/z 338. 1H NMR(DMSO-d6)δ: 9.76,s,2H,NH; 7.11,d,2H,ArH; 6.58,d,2H,ArH; 4.15,s,2H,CH2—N; 4.05,q,2H,CH2—O; 2.93,s,3H,CH3—N; 1.92,s,3H,CH3CO; 1.14,t,3H,CH3—C.

Workup

  1. customcould evaporate over a 24 hr period
  2. customThe product was collected
  3. washwashed with isopropyl alcohol
  4. customto give 1.32 g (3.9 mmol, 78%), mp 162° dec

Sources & evidence

ORD record
ord-8c75a30a6b4b4cd28384004bb524faaa
Source dataset
uspto-grants-2001_10
Patent number
US06306570B1

Reaction notes

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