Acetic Acid → HCID 15671167, compound

HRID 2351506Notes

Reaction equation

Cl[CH:2]([C:28]([O:30]CC)=O)[CH2:3][C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2([CH3:25])[CH2:19][C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:21]([O:23]C)=[O:22])[CH:16]=3)[O:11]2)=[CH:6][CH:5]=1.[NH2:33][C:34](N)=[S:35].S1(CC[CH2:41][CH2:40]1)(=O)=O.Cl.C(O)(=[O:47])C>>[O:47]=[C:34]1[NH:33][C:28](=[O:30])[CH:2]([CH2:3][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]3([CH3:25])[CH2:19][C:18](=[O:20])[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:21]([O:23][CH2:40][CH3:41])=[O:22])[CH:16]=4)[O:11]3)=[CH:26][CH:27]=2)[S:35]1

Participants

Reactant 5

HCID 176Acetic Acid

HCID 313Hydrochloric Acid

HCID 31347Sulfolane

HCID 2723790Thiourea

HCID 15671151HCID 15671151, compound

Product 1

HCID 15671167HCID 15671167, compound

Procedure

A procedure similar to that described in Example 1 was repeated, except that 4.7 g of methyl 2-[4-(2-chloro-2-ethoxycarbonylethyl)phenoxymethyl]-2-methyl-4-oxochroman-6-carboxylate (prepared as described in Preparation 45), 1 g of thiourea, 10 ml of sulfolane, 15 ml of acetic acid and 15 ml of 3N aqueous hydrochloric acid were used, to afford a crude 6-carboxylic acid corresponding to the title compound. This acid was treated, without purification, with 20 ml of ethanol and 2 ml of a 4N solution of hydrogen chloride in dioxane, following a procedure similar to that described in Preparation 43, to afford 2.7 g of the title compound as a pale yellow glassy substance.

Sources & evidence

ORD record: ord-efc79247dcc148ba9d2e072c5537f336
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04873255

Reaction notes

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