Dimethylformamide dimethyl acetal → [3-(3-Dimethylaminomethylene-thioureido)-propyl]-carbamic Acid tert-butyl Ester

HRID 2119583Notes

Reaction equation

HRID 2119583 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[S:13])([CH3:4])([CH3:3])[CH3:2].CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>>[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([N:14]=[CH:18][N:19]([CH3:21])[CH3:20])=[S:13])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 20616909tert-Butyl 3-thioureidopropylcarbamate

Product 1

HCID 72965844[3-(3-Dimethylaminomethylene-thioureido)-propyl]-carbamic Acid tert-butyl EsterYield 90%

Conditions

Temperature
100 °C

Procedure

A mixture of 1.48 g (6.35 mmol) (3-Thioureido-propyl)-carbamic acid tert-butyl ester and 15 ml Dimethylformamide dimethyl acetal was heated to 100° C. for 16 h. The mixture was concentrated and the residue was purified by flash column chromatography on silica eluting with ethyl acetate/n-hexane 1/1 to yield 1.65 g (90%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash column chromatography on silica eluting with ethyl acetate/n-hexane 1/1

Sources & evidence

ORD record
ord-3f550b4ed4cc4b4e93e61486370bed76
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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