Ammonia → Cyclohexyl isocyanate

HRID 1701968Notes

Reaction equation

HRID 1701968 reaction equation
[CH2:1]([CH:5]1[CH:10](C)[CH2:9][CH2:8][NH:7][C:6]1=[O:12])[CH2:2]CC.C1(CCN=C=O)C=CC=CC=1.ClS(O)(=O)=O.N.[CH2:30]([CH:34]1[CH:39]([CH3:40])[CH2:38][CH2:37][N:36]([C:41]([NH:43][CH2:44][CH2:45][C:46]2[CH:51]=[CH:50][C:49]([S:52]([NH2:55])(=[O:54])=[O:53])=[CH:48][CH:47]=2)=[O:42])[C:35]1=[O:56])[CH2:31][CH2:32][CH3:33]>CO>[CH:8]1([N:7]=[C:6]=[O:12])[CH2:2][CH2:1][CH2:5][CH2:10][CH2:9]1.[CH2:30]([CH:34]1[CH:39]([CH3:40])[CH2:38][CH2:37][N:36]([C:41]([NH:43][CH2:44][CH2:45][C:46]2[CH:51]=[CH:50][C:49]([S:52]([NH:55][C:6]([NH:7][CH:8]3[CH2:2][CH2:1][CH2:5][CH2:10][CH2:9]3)=[O:12])(=[O:53])=[O:54])=[CH:48][CH:47]=2)=[O:42])[C:35]1=[O:56])[CH2:31][CH2:32][CH3:33]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 24638Chlorosulfonic acid3×HCID 160602Phenethyl isocyanateHCID 20504592HCID 20504592, compoundHCID 20504613HCID 20504613, compound

Product 2

HCID 18502Cyclohexyl isocyanateHCID 20504636HCID 20504636, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-butyl-4-methyl-2-oxo-piperidine (m.p. 95°-98° C., prepared according to German Offenlegungsschrift No. 1,023,464) is converted according to Example 2 with phenylethyl-isocyanate to 3-butyl-4-methyl-2-oxo-piperidine-1-(N-2-phenylethyl)-carboxamide, this crude product is converted with chlorosulfonic acid to the sulfochloride, the sulfochloride is converted with ammonia to 4-(2-[3-butyl-4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonamide, m.p. 165°-167° C., from which there is obtained with cyclohexyl isocyanate with N-(4-[2-(3-butyl-4-methyl-2-oxo-piperidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea, m.p. 123°-125° C. (from methanol).

Sources & evidence

ORD record
ord-530b3e03dced45ee8bd2946676a3dc81
Source dataset
uspto-grants-1983_04
Patent number
US04379785

Reaction notes

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