Acetic Acid → HCID 90055151, compound

HRID 1772924Notes

Reaction equation

HRID 1772924 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:8][C:9]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:10]=1[CH:11]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl[S:37]([N:40]=[C:41]=[O:42])(=[O:39])=[O:38].[Cl-].[Al+3].[Cl-].[Cl-]>>[Cl:17][C:15]1[CH:14]=[CH:13][C:10]([CH2:11][N:1]2[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:37](=[O:39])(=[O:38])[NH:40][C:41]2=[O:42])=[C:9]([F:8])[CH:16]=1

Participants

7

Reactant 6

HCID 176Acetic AcidHCID 6115AnilineHCID 70918Chlorosulfonyl isocyanateHCID 27249084-Chloro-2-fluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 90055151HCID 90055151, compoundYield 41%

Procedure

The title compound (4.2 g, 12.3 mmol) was prepared in two steps from aniline (8.8 g, 94.7 mmol), 2-fluoro-4-chlorobenzaldehyde (9.0 g, 63.0 mmol), glacial acetic acid (11.36 g, 183 mmol) and sodium triacetoxyborohydride (20.0 g, 94.5 mmol); followed by chlorosulfonylisocyanate (4.3 g, 30.0 mmol) and aluminium chloride (4.78 g, 35.7 mmol) using the methods of (IntE1).

Sources & evidence

ORD record
ord-348fcba280fa451aa6f57f6171f12029
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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