2-Bromopropane → Isopropyl 5-{1-ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine-3-acetate sesquihydrate

HRID 2107177Notes

Reaction equation

HRID 2107177 reaction equation
[CH2:1]([O:3][C:4]([C:6](=[C:22]1[S:26][C:25](=[S:27])[N:24]([CH2:28][C:29]([OH:31])=[O:30])[C:23]1=[O:32])[C:7]1[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[S:10][CH:11]=1)=[O:5])[CH3:2].[CH:33](Br)([CH3:35])[CH3:34].C(N(CC)CC)C>CN(C)P(=O)(N(C)C)N(C)C>[OH2:3].[CH2:1]([O:3][C:4]([C:6](=[C:22]1[S:26][C:25](=[S:27])[N:24]([CH2:28][C:29]([O:31][CH:33]([CH3:35])[CH3:34])=[O:30])[C:23]1=[O:32])[C:7]1[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:14])[S:10][CH:11]=1)=[O:5])[CH3:2].[OH2:3].[OH2:3].[CH:33]([O:30][C:29](=[O:31])[CH2:28][N:24]1[C:23](=[O:32])[C:22](=[C:6]([C:7]2[N:8]=[C:9]([NH:12][C:13]([NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:14])[S:10][CH:11]=2)[C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:26][C:25]1=[S:27])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 8471TriethylamineHCID 541363965-{1-Ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine acetic acid

Product 1

HCID 131716427Isopropyl 5-{1-ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine-3-acetate sesquihydrate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

Following a procedure similar to that described in Example 27, the desired compound was prepared from 1 g of 5-{1-ethoxycarbonyl-1-[2-(3-phenylureido)thiazol-4-yl]methylene}rhodanine-3-acetic acid, 0.5 g of isopropyl bromide, 0.25 g of triethylamine and 10 ml of hexamethylphosphoric triamide. The resulting yellow crystalline product had the following physical properties.

Sources & evidence

ORD record
ord-78c15ff8f028446296bb6eb3e7a1d3c6
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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