Triethylamine → N,N-Dimethyl-N′-[3-[[(methylamino)carbonyl]oxy]phenyl]thiourea

HRID 1973182Notes

Reaction equation

HRID 1973182 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1)=[S:4].C(OCC)(=O)C.[CH3:20][N:21]=[C:22]=[O:23].C(N(CC)CC)C>CCCCCC>[CH3:1][N:2]([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:22](=[O:23])[NH:21][CH3:20])[CH:7]=1)=[S:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 12228Methyl IsocyanateHCID 5368133Thiourea, N'-(3-hydroxyphenyl)-N,N-dimethyl-

Product 1

HCID 21493114N,N-Dimethyl-N′-[3-[[(methylamino)carbonyl]oxy]phenyl]thiourea

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

1,1-dimethyl-3-(meta-methylcarbamoyloxyphenyl)-2 -thiourea is prepared by charging to a suitable equipped reaction vessel about 32.7 parts by weight of 1,1-dimethyl-3-(meta-hydroxyphenyl)-2-thiourea, about 100 parts by weight of ethyl acetate, about 12 parts by weight of methyl isocyanate and about 1 part by weight triethylamine, refluxing for about 1 hour with stirring, diluting the resulting slurry with about 100 parts by weight of hexane, cooling to about 20° C., recovering the precipitate from the remainder by filtration, washing the recovered solid with ethyl acetate and hexane and air drying.

Workup

  1. customa suitable equipped
  2. customrecovering the precipitate from the remainder
  3. filtrationby filtration
  4. washwashing the recovered solid with ethyl acetate and hexane and air
  5. customdrying

Sources & evidence

ORD record
ord-54392a9588c14b6691541cb84e5ab53e
Source dataset
uspto-grants-1976_12
Patent number
US03996275

Reaction notes

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