Benzyl Bromide → 3-Allylamino-4-phenyl-5-sulfamylbenzoic acid

HRID 1605578Notes

Reaction equation

N[C:2]1[CH:3]=C(C=C([N+]([O-])=O)[C:10]=1C1C=CC=CC=1)C(O)=O.C(Br)C1C=CC=CC=1.[NH2:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([S:44](=[O:47])(=[O:46])[NH2:45])[C:37]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]([OH:34])=[O:33].C(Br)C=C>>[CH2:3]([NH:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([S:44](=[O:47])(=[O:46])[NH2:45])[C:37]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]([OH:34])=[O:33])[CH:2]=[CH2:10]

Participants

Reactant 4

HCID 7498Benzyl Bromide

HCID 7841Allyl bromide

HCID 124087693-Amino-5-nitro-4-phenylbenzoic acid

HCID 215468413-Amino-4-phenyl-5-sulfamylbenzoic acid

Product 1

HCID 215468283-Allylamino-4-phenyl-5-sulfamylbenzoic acid

Procedure

By replacing in Example 1, step D, 3-amino-5-nitro-4-phenylbenzoic acid and benzyl bromide with equimolar amounts of 3-amino-4-phenyl-5-sulfamylbenzoic acid and allyl bromide respectively, and following the procedure described, 3-allylamino-4-phenyl-5-sulfamylbenzoic acid is obtained with a melting point of 169°-172.5° C.

Sources & evidence

ORD record: ord-627eb7b77fe24a48bcf4845430ec63de
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03950380

Reaction notes

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