m-Tolyl isocyanate → HCID 20097119, compound

HRID 1769724Notes

Reaction equation

[NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][S:18][C:17]([CH3:22])([CH3:21])[CH2:16]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:23][C:24]1[CH:25]=[C:26]([N:30]=[C:31]=[O:32])[CH:27]=[CH:28][CH:29]=1>>[CH3:21][C:17]1([CH3:22])[CH2:16][N:15]([C:13](=[O:14])[CH2:12][N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3](=[O:4])[CH2:2][NH:1][C:31]([NH:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([CH3:23])[CH:25]=2)=[O:32])[CH2:20][CH2:19][S:18]1

Participants

Reactant 2

HCID 69303m-Tolyl isocyanate

HCID 20097115HCID 20097115, compound

Product 1

HCID 20097119HCID 20097119, compoundYield 62.8%

Procedure

The procedure is analogous to that described in Example 81, but 0.7 g of 2-amino-N-[2-(2,2-dimethylthiomorpholino)-2-oxoethyl]-N-phenylacetamide and 0.28 g of 3-methylphenyl isocyanate are used as the starting material. After recrystallization from an ethyl acetate/acetonitrile mixture (80/20 by volume), 0.6 g of N-[2-(2,2-dimethylthiomorpholino)-2-oxoethyl]-2-[3-(3-methylphenyl)ureido]-N-phenylacetamide melting at 186° C. is obtained.

Workup

customAfter recrystallization from an ethyl acetate/acetonitrile mixture (80/20 by volume)

Sources & evidence

ORD record: ord-18b165aa1a0845b5910cef29a322e7a8
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382590

Reaction notes

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