Ethyl isocyanate → 1-(6-Ethoxycarbonyl-2-benzothiazolyl)-3-ethylurea

HRID 9136Notes

Reaction equation

HRID 9136 reaction equation
C(C1C=CC2N=C(N[C:16]([NH:18][CH2:19][CH3:20])=[O:17])SC=2C=1)C1C=CC=CC=1.[NH2:23][C:24]1[S:25][C:26]2[CH:32]=[C:31]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:30]=[CH:29][C:27]=2[N:28]=1.C(N(CC)CC)C.C(N=C=O)C>C1(C)C=CC=CC=1>[CH2:36]([O:35][C:33]([C:31]1[CH:30]=[CH:29][C:27]2[N:28]=[C:24]([NH:23][C:16]([NH:18][CH2:19][CH3:20])=[O:17])[S:25][C:26]=2[CH:32]=1)=[O:34])[CH3:37]

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 601008Ethyl 2-Aminobenzothiazole-6-carboxylateHCID 219856141-(6-Benzyl-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219855801-(6-Ethoxycarbonyl-2-benzothiazolyl)-3-ethylureaYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to the General Procedure for 1-(6-substituted-2-benzothiazolyl)-3-ethylurea compounds, and similar to the synthesis of 1-(6-benzyl-2-benzothiazolyl)-3-ethylurea, a mixture of 2-amino-6-ethoxycarbonyl-benzothiazole, triethylamine and ethyl isocyanate in toluene was reacted to give the desired compound 2.40 g (82%). LC/MS 294.0 (M+1); LC retention time 4.29 min.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-193af041f89c4a718cbabf830a9304dc
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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