Phenyl Isothiocyanate → HCID 10479095, compound

HRID 1757128Notes

Reaction equation

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

Participants

Reactant 3

HCID 7673Phenyl Isothiocyanate

HCID 1967957-Amino-3-(2-bromoethoxy)-4-chloroisocoumarin

HCID 2723790Thiourea

Product 1

HCID 10479095HCID 10479095, compoundYield 59%

Procedure

7-(Phenylthiocarbamoylamino)-4-chloro-3-(2-bromoethoxy) isocoumarin was prepared from the reaction of phenyl isothiocyanate with 7-amino-4-chloro-3-(2-bromoethoxy) isocoumarin, yield 59%, m.p. 157°-158° C.; mass spectrum m/e=361 (M+ -PhNH+ 1). Anal. Calc.: C, 48.36; H, 3.39. Found: C, 48.26; H, 3.40. The bromoethoxy compound was then reacted with thiourea by the same procedure to give the final product, yield 32%; mass spectrum (FAB+) m/e 449 (M+ --Br).

Sources & evidence

ORD record: ord-ac92091b3fcc45fcb3da5c2ce5d8cf7a
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05444042

Reaction notes

Loading…