Sodium Bicarbonate → 1-(6-(4-Chlorophenyl)-2-benzothiazolyl)-3-ethylurea

HRID 9148

Reaction equation

HRID 9148 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](OB(O)O)=[CH:20][CH:19]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:16]=[CH:15][C:5]3[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=3[CH:3]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 17810664p-Chlorophenylboric acidHCID 219855641-(6-Bromo-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219856181-(6-(4-Chlorophenyl)-2-benzothiazolyl)-3-ethylureaYield 18%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

Similar to the synthesis of 1-(6-(4-pyrrazolyl)-2-benzothiazolyl)-3-ethylurea, a mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, 4-chlorophenylboric acid, sodium bicarbonate, and Pd(PPh3)4 in DMF/water mixed solvent (5/1) was reacted to give the desired compound 0.020 g (18%). LC/MS 330 (M−1); LC retention time 2.70 min.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-60da8dac3f014ed1b9238d03474e7f55
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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