Methyl Isocyanate → 1-(1,1-Dimethylethyl)-3-methyl-1-(3,3,3-trichloro-2-hydroxypropyl)urea

HRID 127951Notes

Reaction equation

HRID 127951 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH:7]([OH:12])[C:8]([Cl:11])([Cl:10])[Cl:9])([CH3:4])[CH3:3].[CH3:13][N:14]=[C:15]=[O:16]>C(Cl)(Cl)Cl>[CH3:4][C:2]([N:5]([CH2:6][CH:7]([OH:12])[C:8]([Cl:11])([Cl:10])[Cl:9])[C:15]([NH:14][CH3:13])=[O:16])([CH3:1])[CH3:3].[CH3:4][C:2]([N:5]([CH2:6][CH:7]([O:12][C:15](=[O:16])[NH:14][CH3:13])[C:8]([Cl:11])([Cl:10])[Cl:9])[C:15]([NH:14][CH3:13])=[O:16])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 234710203-(Tert-butylamino)-1,1,1-trichloropropan-2-ol

Product 2

HCID 234710181-(1,1-Dimethylethyl)-3-methyl-1-(3,3,3-trichloro-2-hydroxypropyl)ureaHCID 234710191-(1,1-Dimethylethyl)-3-methyl-1-[3,3,3-trichloro-2-(methylcarbamoyloxy)propyl]urea

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The reaction of 3-(1,1-dimethylethylamino)-1,1,1-trichloro-2-propanol with methyl isocyanate normally takes place at -70° to +80° C. in an inert solvent such as chloroform to produce 1-(1,1-dimethylethyl)-3-methyl-1-(3,3,3-trichloro-2-hydroxypropyl)urea and 1-(1,1-dimethylethyl)-3-methyl-1-[3,3,3-trichloro-2-(methylcarbamoyloxy)propyl]urea.

Sources & evidence

ORD record
ord-58cfff0211dc4dedbf7f1af58ace5c0d
Source dataset
uspto-grants-1981_03
Patent number
US04258060

Reaction notes

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