Ethyl isocyanate → Ethyl 4-(3-ethylureido)-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate

HRID 982231Notes

Reaction equation

HRID 982231 reaction equation
Cl.[NH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[C:5]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:18][CH:17]=2)[CH:4]=1.[CH2:34](N(CC)CC)[CH3:35].[CH2:41]([N:43]=[C:44]=[O:45])[CH3:42]>C(Cl)Cl>[CH2:41]([NH:43][C:44](=[O:45])[NH:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([O:11][CH2:34][CH3:35])=[O:10])=[C:5]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:18][CH:17]=2)[CH:4]=1)[CH3:42]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 679444774-Amino-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate hydrochloride

Product 1

HCID 15106501Ethyl 4-(3-ethylureido)-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 200 mg of ethyl (4-amino-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate hydrochloride, 40.5 mg of triethylamine and 5 mg of methylene chloride was added 30 mg of ethyl isocyanate followed by stirring at room temperature overnight. The reaction mixture was treated in a manner similar to Example 68 to obtain 130 mg of ethyl 4-(3-ethylureido)-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetate.

Workup

  1. additionThe reaction mixture was treated in a manner similar to Example 68

Sources & evidence

ORD record
ord-644d20d173484364bbff9de7b8d5261b
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

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