Benzoic acid, 3-isothiocyanato- → HCID 10413552, compound

HRID 1110073Notes

Reaction equation

HRID 1110073 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]=[C:11]=[S:12])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].[NH2:13][C:14]1[CH:24]=[C:23]2[C:17]([C:18]([Cl:29])=[C:19]([O:25][CH2:26][CH2:27][Br:28])[O:20][C:21]2=[O:22])=[CH:16][CH:15]=1.NC(N)=S>>[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH:13][C:14]2[CH:24]=[C:23]3[C:17]([C:18]([Cl:29])=[C:19]([O:25][CH2:26][CH2:27][Br:28])[O:20][C:21]3=[O:22])=[CH:16][CH:15]=2)=[S:12])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 75046Benzoic acid, 3-isothiocyanato-HCID 1967957-Amino-3-(2-bromoethoxy)-4-chloroisocoumarinHCID 2723790Thiourea

Product 1

HCID 10413552HCID 10413552, compoundYield 64%

Procedure

7-(m-Carboxyphenylthiocarbamoylamino)-4-chloro-3-(2-bromoethoxy)isocoumarin was prepared from the reaction of m-carboxyphenyl isothiocyanate with 7-amino-4-chloro-3-(2-bromoethoxy)isocoumarin, yield 64%, m.p. 157°-158° C.; mass spectrum m/e 361 (M+ -(COOH)PhNH+1). Anal. Calc.: C, 45.85; H, 2.84. Found: C, 45.73; H, 2.86. The bromoethoxy compound was then reacted with thiourea to give the product, yield 21%; mass spectrum (FAB+) m/e 493 (M+ -Br).

Workup

  1. customto give the product, yield 21%

Sources & evidence

ORD record
ord-6c29e8bc644d49728442fb31b7732755
Source dataset
uspto-grants-1994_06
Patent number
US05324648

Reaction notes

Loading…