Tetramethyl orthocarbonate → 6-(1-Butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-2-hydroxybenzimidazole

HRID 276082Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.220 mg of N-1-butanesulfonyl-4-amino-3-(2,4-dichlorobenzylamino)benzamide, 0.3 ml of tetramethoxymethane and 2.0 ml of acetic acid was stirred at 60° C. for 4 hours. Acetic acid was distilled off under reduced pressure, and the residue was extracted with chloroform and with water. The chloroform layer was concentrated, and 4.0 ml of methanol and 36% hydrochloric acid (4 drops) were added to the residue. The mixture was stirred at 60° C. for 2 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The crystals precipitated were washed with water, and were dried to give 0.207 g of 6-(1-butanesulfonylcarbamoyl)-1-(2,4-dichlorobenzyl)-2-hydroxybenzimidazole (379).

Workup

distillationAcetic acid was distilled off under reduced pressure
extractionthe residue was extracted with chloroform and with water
concentrationThe chloroform layer was concentrated
addition4.0 ml of methanol and 36% hydrochloric acid (4 drops) were added to the residue
stirringThe mixture was stirred at 60° C. for 2 hours
customThe crystals precipitated
washwere washed with water
customwere dried

Sources & evidence

ORD record: ord-faf80ac69ee141c385ac07307c3a6662
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352985B1

Reaction notes

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